The method of obtaining compounds (foradil)borane and the method of deriving tetrakis (foradil)borate

 

(57) Abstract:

The method of obtaining (foradil)borane General formula (3), where each of R1- R5is a hydrogen atom, fluorine atom, alkyl group or alkoxygroup, and if at least one of R1- R5is a fluorine atom, XINis a fluorine atom, bromine, chlorine or iodine, and n is 2 or 3, including interaction ferrimagnetic derivative of General formula (1), where R1- R5described above, and Xandis a chlorine atom, bromine or iodine, boron halide of General formula (2): where XINas described above, in a solvent (a) containing diethyl ether and/or tetrahydrofuran, and the solvent (C) having a higher boiling point than diethyl ether and tetrahydrofuran, wherein the interaction ferrimagnetic derivative and boron halide is carried out in a solvent (a) and then adding the reaction solution to the solvent (b), heated to 80°C and above, followed by distillation of the solvent (a). Also described is a method of obtaining derived tetrakis(foradil)borate. The technical result is simplification. 6 C. and 27 C.p. f-crystals.

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The present isoperibolic halide, employees, for example, as useful socialization for metallocene catalyst (polymerization catalyst) used in the reaction complex of cationic polymerization, and to a method of deriving tetrakis(foradil) borate.

The background to the invention

Connection (foradil)borane, in particular Tris(pentafluorophenyl) borane, is a useful compound as socializaton for promotion of the activity of the metallocene catalyst (polymerization catalyst) used in the reaction complex of cationic polymerization, and recently metallocene catalyst has attracted considerable attention as a catalyst for polymerization of olefins.

An example of a method of obtaining the above-mentioned Tris(pentafluorophenyl)borane disclosed in Proc. Chem. Soc., 1963 (July), 212. More precisely, panafcortelone, produced by the interaction of bromopentafluorobenzene with n-butyllithium (n-BuLi), reacts with trichloride boron and, as a consequence, Tris (pentafluorophenyl)borane. However, in this method, the reaction system must be cooled to -78othat makes this method unsuitable for industrial use.

For solutions in the method of producing Tris(pentafluorophenyl)borane. In accordance with this method, for example, pentafluorophenyl magnesium bromide and diethylether of boron TRIFLUORIDE interact with each other in a chain ether solvent. So, it is not necessary to cool the reaction system to -78oC, making this the preferred method compared to the above reaction.

Further, Japanese Laid-Open Patent Application N 199871/1994 (Tokukaihei 6-199871) discloses a method of obtaining triarylmethane when interacting derived arulmani of halide from a halide of boron in the chain ether solvent or a mixed solvent consisting of a chain ether solvent and an aromatic hydrocarbon solvent. The above publication also discloses a method for separation and removal of the magnesium halide produced as a by-product of the target product, namely trainborne.

Derived tetrakis(foradil)borane is also a useful connection, as mentioned above socializaton. For example, Japanese Laid-Open Patent Application N 247980/1994 (Tokukaihei 6-247980) discloses a method of deriving tetrakis(pentafluorophenyl) borate as a kind of derived tetrakis(foradil)borane. More precisely, the disclosed method of interaction of proizvodi naftifine)borane. When used in the above-mentioned method of boron halide, along with the desired product, namely a derivative of Tris(pentafluorophenyl)borane, as a by-product formed magnesium halide.

However, because the above-mentioned conventional methods use the chain ether solvent having a relatively low boiling point, such as diethyl ether, the reaction system must be cooled. So, in order to obtain the compound (foradil)borane for industrial use, the necessary cooling apparatus, etc., moreover, diethyl ether is extremely flammable. In addition, in the above-mentioned conventional methods are so difficult to control the reaction that produces a by-product, such as Quaternary boron compound type derived tetrakis(foradil) borate. This makes it difficult for selective connection (foradil)borane, such as Tris(foradil)borane and bis(foradil)boryl halide. In addition, a chain ether solvent is usually more expensive than the cyclic ether solvent.

Thus, the problem of the above-mentioned conventional methods is that they are difficult to apply to industrial use, in other words, nran and bis(foradil)boryl halide, of which allocate and delete obtained as a by-product of a magnesium halide, there can be obtained selectively, in a simple way and at low cost. The use of a cyclic ether solvent in the above-mentioned conventional methods, triggers unwanted side reactions such as polymerization of cyclic ether solvent with a ring opening. In addition, the use of only an aromatic hydrocarbon solvent in the above-mentioned conventional methods reduces the output connection (foradil)borane, such as Tris(foradil)borane and bis(foradil)boryl halide.

On the other hand, when the halide of magnesium remains in the connection (foradil)borane used as socializaton for metallocene catalyst, metallocene catalyst loses its activity. Thus, when the above compound or a derivative thereof is used as the above-mentioned socializaton obtained as a by-product halide of magnesium must be separated and removed.

However, since the solubility derived tetrakis(pentafluorophenyl) borate and magnesium halide solvents are practically the same, to share their Messiah.) borate byproduct, namely, the halide of magnesium, cannot be easily separated and removed from the desired product, namely the derivative of arakis(foradil) borate. Thus, the problem of the above-mentioned conventional method of deriving tetrakis(foradil) Borat is that it is impossible to derive tetrakis(foradil) borate, which is separated and removed by-product, namely the halide of magnesium.

The method of deriving ferrimagnet, which is an intermediate in the production method of a derivative tetrakis(florally)borate, disclosed, for example, in J. Org.Chem., 29, 2385 (1964). More precisely, alkylamine derived as etimani bromide (EtMgBr), was added dropwise to a solution obtained by dissolving pentafluorobenzoyl in ethereal solvent such as tetrahydrofuran (THF), to initiate the reaction of EtMgBr-pentafluorobenzoyl. Then, as a kind of derived ferrimagnet obtained derived panafcortelone. Japanese Laid-Open Patent Application N 247976/1994 (Tokukaihei 6-247976) discloses another method of obtaining. In this way derived panafcortelone get when prikatyvanie solution obtained by dissolving pentafluorobenzoyl in the ether solvent, the other solution obtained by shmesani nilmini receive exchange reaction, in which the alkyl group is derived alkaline replaced pentafluorophenyl group.

However, in order to derive tetrakis (pentafluorophenyl) borate according to the above method, alkylamine derivative gain in the first stage, the above-mentioned exchange reaction to obtain a derived panafcortelone conducted in the second stage, and derived panafcortelone interacts with the boron compound at the third stage. In other words, because alkylamine derived and derived panafcortelone receive separately before derivatization tetrakis (pentafluorophenyl)borate, the reaction is carried out in three stages. Thus, the problem is that the above methods cannot effectively derive tetrakis (pantpthenic)borate simple way.

Brief description of the invention

Therefore, the first aim of the present invention is the provision of a method of obtaining compound (foradil)borane, such as Tris(foradil)borane and bis(foradil)boryl halide, which is separated and removed as a by-product of a magnesium halide, selectively, in a simple manner and with low Tatralandia (foradil)borane and found the magnesium halide produced as a by-product together with the connection (foradil)borane, falls out of the reaction system and is deposited and that the connection (foradil)borane can be obtained selectively, low-cost, simple way:

(1) the interaction derived ferrimagnet with the boron halide in a solvent (a) containing diethyl ether and/or tetrahydrofuran;

(2) adding the reaction solution to the solvent (b) having a higher boiling point than diethyl ether and/or tetrahydrofuran, whereas diethyl ether and/or tetrahydrofuran is distilled off. In other words, the inventors found that the compound (foradil)borane, such as Tris(foradil)borane and bis (foradil)boryl halide, which is separated and removed as a by-product of a magnesium halide, can be obtained selectively, in a simple way and at low cost when adopting the above method.

That is, for the first purpose, the method of obtaining compounds (foradil)borane present invention relates to a method for obtaining compounds (foradil)borane expressed General formula (3)

...

where each of R11-R5is a fluorine atom, Xbis a fluorine atom, chlorine atom, bromine atom or iodine atom, and n is 2 or 3, and the above-mentioned method is characterized by interaction

derived ferrimagnet expressed General formula (1)

...

where each of R1-R5is a hydrogen atom, a fluorine atom, a hydrocarbon group or alkoxygroup, while at least one of R1-R5is a fluorine atom, Xais a chlorine atom, a bromine atom or an iodine atom, a boron halide expressed by General formula (2):

...

where Xbis a fluorine atom, chlorine atom, bromine atom or iodine atom, in a solvent (a) containing diethyl ether and/or tetrahydrofuran, and then adding the resulting reaction solution to the solvent (b) having a higher boiling point than diethyl ether and/or tetrahydrofuran, and distillation of diethyl ether and/or tetrahydrofuran.

To implement the above first objective, the method of obtaining compounds (foradil)borane present invention relates to a method for obtaining compounds (foradil)borane expressed above General formula (3 (1), with the boron halide expressed by the above General formula (2) in the solvent (c) containing diethyl ether and/or tetrahydrofuran and connection with a higher boiling point than diethyl ether and/or tetrahydrofuran, and then distillation of diethyl ether and/or tetrahydrofuran from the reaction solution.

The magnesium halide is not soluble in the solvents (listed below), except as diethyl ether and tetrahydrofuran. In contrast, compound (foradil)borane dissolved in solvents including diethyl ether and tetrahydrofuran. In other words, the magnesium halide and the compound (foradil)borane dissolved in solvents, with the exception of diethyl ether and tetrahydrofuran, with different solubility. Thus, in accordance with the above method, since diethyl ether and/or tetrahydrofuran is distilled off from the reaction system, the magnesium halide produced as a by-product together with the connection (foradil)borane, falls out of the reaction system and deposited. In short, the magnesium halide produced as a by-product can be separated and removed. In accordance with the above method, since the reaction is easily controlled, ( solvents, such as a cyclic ether solvents, which is relatively easy to apply. Also, because the resulting compound (foradil)borane, such as Tris(foradil)borane and bis(foradil)boryl halide, does not form a complex, and Quaternary compounds, compound (foradil)borane can be easily cleaned. As a result, it is possible to obtain compound (foradil)borane, such as Tris(foradil)borane and bis(foradil)boryl halide from which the magnesium halide produced as a by-product is separated and removed selectively, in a simple way at low cost. Thus, the present method of obtaining has the advantage compared to conventional methods for industrial use and makes it possible to obtain compound (foradil)borane, which separates and removes the magnesium halide, high yield and selectivity.

The second purpose of the present invention is the provision of a method of deriving tetrakis (foradil)borate, which separates and removes the magnesium halide produced as a by-product, in a simple way at low cost.

The inventors of the present invention conducted a thorough investigated the)borate, which separates and removes the magnesium halide produced as a by-product, can be obtained in a simple manner at low cost when interacting compounds (foradil)borane obtained when adopting the above method, with the derived ferrimagnet and completed the present invention.

To be more precise, for the implementation of the above-mentioned second objective, the method of deriving tetrakis(foradil)borate present invention relates to a method for deriving tetrakis(foradil)borate, expressed the General formula (5):

...

where each of R1-R10is a hydrogen atom, a fluorine atom, a hydrocarbon group or alkoxygroup, while at least one of R1-R5and one of R6-R10is a fluorine atom, Xcis a chlorine atom, a bromine atom or an iodine atom, and n is 2 or 3, and the above method is characterized by the interaction of the compounds (foradil)borane obtained by the above method, with the derived ferrimagnet expressed by the General formula (4):

...

where each of R6-R10is a hydrogen atom, a fluorine atom, a hydrocarbon group iecsa a chlorine atom, a bromine atom or an iodine atom.

According to the above method, it became possible to derive tetrakis(foradil)borate, which separates and removes the magnesium halide produced as a by-product when the connection (foradil)borane, simple manner at low cost.

To implement the above second objective way of deriving tetrakis(foradil)borate present invention relates to a method for deriving tetrakis(foradil)borate, expressed the General formula (10):

...

where each of R2-R4and R6-R10is a hydrogen atom, a fluorine atom, a hydrocarbon group or alkoxygroup, while at least one of R6-R10is a fluorine atom, Xcis a chlorine atom, a bromine atom or an iodine atom, a n is 2 or 3, and this method is characterized

(A) the interaction of the aryl fluoride expressed General formula (6):

...

where each of R2-R4is a hydrogen atom, a fluorine atom, a hydrocarbon group or alkoxygroup, halogenated hydrocarbon, expressed the General formula (7):

RoXa...

where each of R2-R4is a hydrogen atom, a fluorine atom, a hydrocarbon group or alkoxygroup and Xais a chlorine atom, a bromine atom or an iodine atom;

(C) interaction derived ferrimagnet with the boron halide expressed by the above General formula (2);

(C) adding the reaction solution to the solvent (b) having a higher boiling point than diethyl ether and/or tetrahydrofuran;

(D) distillation of diethyl ether and/or tetrahydrofuran to obtain compounds (foradil)borane expressed General formula (9):

...

where each of R2-R4is a hydrogen atom, a fluorine atom, a hydrocarbon group or alkoxygroup and Xbis a chlorine atom, a bromine atom or an iodine atom, and n is 2 or 3;

(E) interaction of the obtained compound (foradil) with borane derivative ferrimagnet expressed by the above General formula (4).

According to the above method one hundred is obtained as a by-product, a simple way at low cost, using as source material the aryl fluoride.

Next, the third objective of the present invention is to provide an efficient method of deriving tetrakis (foradil)borate with low costs is actually by one-step reaction (the so-called reaction in one pot).

The inventors of the present invention conducted a thorough investigation of the method of deriving tetrakis(foradil) borate and found that the derived tetrakis(foradil)borate can be effectively obtained in a simple manner at low cost in the interaction of the aryl fluoride, galogensoderjasimi hydrocarbon and magnesium in an ether solvent (e), or a mixed solvent consisting of ether solvent (e) and the hydrocarbon solvent, to obtain a derivative tetrakis(foradil) borate, and the subsequent interaction derived ferrimagnet with the boron halide or Tris(foradil)borane, in fact, at one stage of the reaction (the so-called reaction in one pot) and completed the present invention.

To be more precise, for the implementation of the third objective of the present invention a method of receiving what about tetrakis(foradil)borate, expressed in the General formula (11):

...

where each of R2-R4is a hydrogen atom, a fluorine atom, a hydrocarbon group or alkoxygroup and Xais a chlorine atom, a bromine atom or an iodine atom, and the above-described method is characterized by the interaction of the aryl fluoride expressed above General formula (6), halogenated hydrocarbon, expressed in the above General formula (7), and magnesium with each other in the ether solvent (e) and the hydrocarbon solvent, to obtain a derivative ferrimagnet expressed above General formula (8), and then the interaction derived ferrimagnet with the boron halide expressed by the above General formula (2).

According to the above method, this reaction can be carried out virtually in a single phase, thus giving the ability to effectively derive tetrakis(foradil)borate simple manner at low cost.

For the third objective of the method of deriving tetrakis(foradil)borate present invention relates to a method for deriving tetrakis(foradil)borate, expressed the General formula (13):

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GPOI or alkoxygroup, while at least one of R11-R25is a fluorine atom, and Xais a chlorine atom, a bromine atom or an iodine atom and the above-described method is characterized (A) by the interaction of the aryl fluoride expressed above General formula (6), halogenated hydrocarbon, expressed in the above General formula (7), and magnesium with each other in the ether solvent (e), or a mixed solvent consisting of ether solvent (e) and the hydrocarbon solvent, to obtain ferrimagnetic derived as expressed in the above General formula (8);

(C) interaction obtained ferrimagnetic derived from Tris(foradil)borane expressed by the General formula (12):

...

where each of R11-R25is a hydrogen atom, a fluorine atom, a hydrocarbon group or alkoxygroup, while at least one of R11-R25is a fluorine atom.

According to the above method, the reaction may proceed in fact, at one stage, thus giving the ability to effectively derive tetrakis(foradil) borate simple manner at low cost. Further, according to the above-described method has made possible the, the knitted with the boron atom has a different structure from the structure of other porarily groups.

Following the chain, the nature and advantages of the invention will be understood from subsequent description. In addition, the effects of the present invention will be explained in the subsequent description.

Description options incarnation

The method of obtaining compounds (foradil)borane expressed above General formula (3), is a way of interacting ferrimagnetic derived as expressed in the above General formula (1) (hereinafter called ferrimagnetism derivative (1)) with the boron halide expressed above General formula (2) (hereinafter called the boron halide (2) in the solvent (a) containing diethyl ether and/or tetrahydrofuran, followed by adding the resulting reaction solution to the solvent (b) having a higher boiling point, than diethyl ether (boiling point: 34,48oC) and/or tetrahydrofuran (boiling point: 66oC), whereas diethyl ether and/or tetrahydrofuran is distilled off.

Also the method of obtaining compounds (foradil)borane expressed above General formula (3), is etilogy ether and/or tetrahydrofuran and connection with a higher boiling point, than diethyl ether and/or tetrahydrofuran, and subsequent distillation of diethyl ether and/or tetrahydrofuran from the reaction solution.

Next, the method of deriving tetrakis(foradil)borate, expressed the General formula (5), is a way of interacting compounds (foradil)borane obtained by the above method, with ferrimagnetism derivative expressed by the above General formula (4) (hereinafter called ferrimagnetism derivative (4)).

Furthermore, the method of deriving tetrakis(foradil)borate, expressed the General formula (10) represents a way:

(A) interaction of the aryl fluoride expressed above General formula (6) (hereinafter called the aryl fluoride (6)), halogenated hydrocarbon, expressed in the above General formula (7) (hereafter referred to as halogenated hydrocarbon (7)), and magnesium in a solvent (a) containing diethyl ether and/or tetrahydrofuran, to obtain ferrimagnetic derived as expressed in the above General formula (8) (hereinafter called ferrimagnetism derivative (8));

(C) interaction obtained ferrimagnets (b), having a higher boiling point than diethyl ether and/or tetrahydrofuran, whereas diethyl ether and/or tetrahydrofuran is distilled off, to obtain compounds (foradil)borane expressed General formula (9);

(D) interaction of the obtained compound (foradil)borane with ferrimagnetism derivative (4).

In the present invention ferrimagnet derivative (1) used as the starting material, is a compound in which each of the substituting groups, denoted as R1-R5is a hydrogen atom, a fluorine atom, a hydrocarbon group or alkoxygroup, while at least one of R1-R5is a fluorine atom, and the replacement group, denoted as Xais a chlorine atom, a bromine atom or an iodine atom.

Also ferrimagnet derivative (4) used in the present invention, is a compound in which each of the substituting groups, denoted as R6-R10is a hydrogen atom, a fluorine atom, a hydrocarbon group or alkoxygroup, while at least one of R6-R10is a fluorine atom, and the replacement group, denoted as Xc, aulet aryl group, alkyl group with a straight chain, branched chain or cyclic alkyl group containing up to 12 carbon atoms, alkenylphenol group with a straight chain, branched chain, or cyclic alkenylphenol group containing 2-12 carbon atoms and so on, the Hydrocarbon group may include, in addition, the functional group remaining inactive in the reactions in the present invention. Examples of such functional groups are: methoxy group, methylthiourea, N, N-dimethylaminopropan or on-anthrope, p-anthrope, trimethylsilyl group, tert - butyldimethylsilyloxy, triptorelin group, etc.

CNS group expressed by General formula (A):

-ORa...

where Rais a hydrocarbon group. Examples of the hydrocarbon group denoted by Rain this formula are: aryl group, an alkyl group with a straight chain, branched chain or cyclic alkyl group containing up to 12 carbon atoms, Alchemilla group with a straight chain, branched chain or cyclic Alchemilla group containing 2-12 carbon atoms. The hydrocarbon group may include, in addition, a functional group, ostau, irarenai the above General formula (A) are: methoxy group, ethoxypropan, n-propoxylate, n-butoxypropyl, isobutoxy, second-butoxypropan, tert-butoxypropan, cyclohexyloxy, alliancegroup, fenoxaprop etc.

Examples ferrimagnetic derivatives (1) and (4) are: panafcortelone chloride, panafcortelone bromide, panafcortelone iodide, 1,2,3,5-tetracarbonylnickel bromide, 1,2,4,5-tetracarbonylnickel chloride, 1,2,4 - triptoreline chloride, 1,3,5-triptoreline iodide, 2,3,5,6-titrator-4-methylphenylamine bromide, 2,5-diperpanjang bromide, 2,5-debtor-3-methylphenylamine chloride, 2,3,4,6 - titrator-5-methylphenylamine bromide, 2,4,6-Cryptor-5 - methylphenylamine chloride, 2,3,5,6-titrator-4-methoxybenzylamine bromide, 2,3,6-Cryptor-5-methoxyphenamine chloride, 2,4,6 - Cryptor-5-methoxyphenamine bromide, 2,5-debtor-3-methoxybenzylamine chloride, 2,5-debtor-4-methoxybenzylamine bromide, 2-performane bromide, 4-performane bromide, 2-fluoro-4 - methylphenylamine bromide, etc. From these examples ferrimagnetic derivative is more preferable panafcortelone bromide. If circumstances require, you can use more than one type of photo is not limited. For example, ferrimagnetic derivatives (1) and (4) can be obtained by the reaction of magnesium and ferril of halide, such as FERRYL chloride, ferril bromide and ferril iodide.

Ferrimagnet derivative expressed by the above General formula (1) in which at least two substituting groups, denoted as R1and R5are fluorine atoms, i.e., ferrimagnetic derivative (8) can be obtained by the interaction of halftoned with fluorine atoms at least in two positions (ortho-positions), the neighboring hydrogen atom, i.e., halftoned (6); halogen-substituted hydrocarbon (7) and magnesium. The method of deriving tetrakis(foradil)borate using halftoned (6) as starting compound will be described below.

The boron halide (2) is a compound that replaces the group of which, denoted by Xbis a fluorine atom, chlorine atom, bromine atom or iodine atom. Examples of the boron halide (2) are boron TRIFLUORIDE, trichloride boron, tribromide boron and triode boron. From all these examples of the most preferred is boron TRIFLUORIDE. If circumstances so require, you can use more than one type of halide morgidrostroy complex.

The solvent (a), mentioned here, is not particularly limited as long as it is non-aqueous solvent which is inactive to the reaction taking place in the present invention, containing diethyl ether and/or tetrahydrofuran, and in which are dissolved ferrimagnetic derivatives (1) and (8), boron halide (2), connection (foradil)borane as the target product, such as Tris(foradil)borane and bis(foradil)boryl halide, and an arbitrary halftoned (6) and halogen-substituted hydrocarbons (7).

The solvent (b), mentioned here, is not particularly limited as long as it is non-aqueous solvent which is inactive to the reaction taking place in the present invention, having a higher boiling point than diethyl ether and/or tetrahydrofuran, and in which the connection (foradil)borane as the target product is dissolved, and the magnesium halide produced as a by-product, is not soluble.

The solvent (c), mentioned here, is not particularly limited as long as it is non-aqueous solvent which is inactive to the reaction taking place in the present invention, containing diethyl ether and/or tetrahydrofuran and connection with a higher point cyprogenia boron (2) and compound (foradil)borane, as the target product, and the magnesium halide produced as a by-product, is not soluble.

The solvent (d), mentioned here, is not particularly limited as long as it is non-aqueous solvent which is inactive to the reaction taking place in the present invention, containing diethyl ether and/or tetrahydrofuran and connection with a higher boiling point than diethyl ether and/or tetrahydrofuran, and in which are dissolved the compound (foradil)borane, ferrimagnet derivative (4) and derived tetrakis(foradil) borate as the target product, and the magnesium halide produced as a by-product, is not soluble.

Although the solvents (a), (c) or (d) is used, and diethyl ether, and tetrahydrofuran, the ratio of these two compounds is not particularly limited. Also the ether solvent and hydrocarbon solvent are preferred as compounds contained in the solvent (b), (c) or (d). The solvent (a) may contain an ether solvent and hydrocarbon solvent (hereinafter referred to as jointly ether and hydrocarbon solvents), if circumstances so require.

Examples afire ether, diisopropyl ether, di-n-butyl ether, Diisobutyl ether, di-n-pentalogy ether, diisopentyl ether, 1,2-dimethoxyethane, 1,2-diethoxyethane and di(2-methoxyethoxy) ether;

cyclic ethers such as tetrahydrofuran and 1,4-dioxane; and so on

Note that this ether solvent include diethyl ether and tetrahydrofuran, and thereafter the ether solvent, diethyl ether and tetrahydrofuran are called jointly ether solvent (e).

Examples of the hydrocarbon solvent include, but are not limited to:

aliphatic hydrocarbons are straight chain, branched chain or cyclic aliphatic hydrocarbons such as n-pentane, isopentane, hexane, cyclohexane, heptane, octane, Nanan, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, octadecane, paraffin and petroleum ether;

aromatic hydrocarbons such as benzene, toluene, o-xylene, m-xylene, p-xylene, 1,2,3-trimethylbenzene, 1,2,4 - trimethylbenzene, 1,2,5-trimethylbenzene, 1,3,5-trimethylbenzene, ethylbenzene, propylbenzene and butylbenzoyl; and so on

Examples of the ether and hydrocarbon solvents, which can suitably be combined with diethyl ether, is in carbon), Dean, octadecan, liquid paraffin, etc. in Addition, examples of the ether and hydrocarbon solvents, which can suitably be combined with the tetrahydrofuran are heptane, octane, IsoparE, Dean, octadecan, liquid paraffin, etc.

You can effectively use one member or a mixture of two or more members selected from these examples of the ether and hydrocarbon solvents. In the methods of manufacturing of the present invention, the cyclic ether can be used as ether and a hydrocarbon solvent. Preferably, the boiling point of the ether and hydrocarbon solvents was 60oC or above, and when used as a solvent (b) 80oC or higher. In other words, it is preferable to heat the solvent (b) up to 80oC or above, so diethyl ether and/or tetrahydrofuran quickly distilled. When the ether and hydrocarbon solvents are a mixture, boiling point means the lowest boiling point of all the mixed compounds. Preferably diethyl ether and tetrahydrofuran, as well as the ether and hydrocarbon solvents, form no azeotrope mixtures.

The ratio of diethyl ether and/or tetrahydrofuran at relationships in homogeneous mix the mixture. However, this ratio preferably is in the range between 1:0 and 1:10 by volume. In short, ether and hydrocarbon solvents can be used up to such an extent that does not cause any undesirable effect in the reactions in the present invention. When the solvent (a) contains ether and hydrocarbon solvents, ether and hydrocarbon solvents can be used up to such an extent that does not cause any undesirable effect in the reactions in the present invention.

The amount of solvent (a) is not particularly limited. For example, preferred is a number, in which the concentration ferrimagnetic derivatives (1) and (8) or boron halide (2) is in the range between 0.1 and 80 weight percent. Method of dissolution ferrimagnetic derivative (1) and one of the halides of boron (2), or both halftoned (6) and halogensubstituted hydrocarbon (7) in the solvent (a) is not particularly limited. In other words, the method of preparing a solution by dissolving ferrimagnetic derivative (1) in solvent (a), a method of preparing a solution by dissolving the boron halide (2) in solvent (a) as Tongo hydrocarbon (7) in the solvent (a) is not particularly limited.

The amount of solvent (b) is not particularly limited and can be used any number of solvent (b), until the connection (foradil)borane or a derivative tetrakis(foradil)borate will completely dissolve in it.

The amount of solvent (c) is not particularly limited. For example, preferred is a number, in which the concentration ferrimagnetic derivative (1) and boron halide (2) is in the range between 0.1 and 80 weight percent. Method of dissolution ferrimagnetic derivative (1) or boron halide (2) in the solvent (c) is not particularly limited. In other words, the method of preparing a solution by dissolving ferrimagnetic derivative (1) in the solvent (c) and method of preparing a solution by dissolving the boron halide (2) in the solvent (c), as circumstances require, is not particularly limited.

The amount of solvent (d) is not particularly limited. For example, preferred is a number, in which the concentration of compounds (foradil)borane or ferrimagnetic derivative (4) is in the range between 0.1 and 80 weight percent. Method of dissolving the compounds (foradil)borane or ferrimagnetic derivative (4) will dissolve in the Rila)borane or ferrimagnetic derivative (4) in the solvent (d) is not particularly limited. In addition, a solution obtained by dissolving compound (foradil)borane in a solvent (d) may be a solution of the compound (foradil) borane prepared using the solvents (a), (b) or (c), i.e. the reaction solution.

The molar ratio ferrimagnetic derivative (1) and boron halide (2) (ferrimagnet derivative (1)/boron halide (2)) is not particularly limited. However, this ratio preferably is in the range between 1.0 and 5.0. The limitation of these limits up to 2.5 and 5.0 inclusive, more preferably up to 2.7 and 4.0 inclusive, and most preferably up to 2.8 and 3.5, inclusive, provides the opportunity to selectively receive a connection (foradil)borane expressed by the above General formula (3) in which n is 3, namely Tris(foradil)borane. Also, limiting molar ratio to range between 1.0 inclusive and 2.5, inclusive, preferably to between 1.2 to 2.4 inclusive, and most preferably to between 1.3 and 2.3, inclusive, provides an opportunity to obtain a connection (foradil)borane expressed by the above General formula (3) in which n is 2, namely bis(foradil)boryl halide as a main product. When Moroni, when the molar ratio is more than 5,0, there are too many unreacted ferrimagnetic derivative (1). When this connection (perioral)borane, such as Tris(foradil)borane and bis(foradil)boryl halide will not be effectively obtained.

A method of mixing a solution prepared by dissolving ferrimagnetic derivative (1) in the solvent (a) or (c) (which is hereinafter referred to as a solution of the magnesium derivative (1)) with another solution prepared by dissolving the boron halide (2) in the solvent (a) or (c) is not particularly limited. However, preferably dropwise, one of the solutions to the other continuously or sequentially. Here, the boron halide (2) can be mixed with a solution of magnesium derivative (1) directly, omitting the preparation of a solution of boron halide (2).

The temperature of the mixture solution of the magnesium derivative (1) with a solution of boron halide (2) is preferably 80oC or below, more preferably in the range between -40oC and 70oC and most preferably in the range between -20oC and 50oC. Because, when the above-mentioned two kinds of solutions are mixed with each other at a temperature of 80oC and is Chou reaction becomes difficult, resulting in reduced yield and selectivity of the compounds (foradil)borane, such as Tris(foradil)borane and bis(foradil)boryl halide. When establishing a mixing temperature below -40oC is not achieved significant effects compared with the case where the temperature of the mixture is set in the above range.

While the solution of the magnesium derivative (1) and a solution of boron halide (2) mixed together and stirred, the reaction between ferrimagnetism derivative (1) and boron halide (2) occurs in the solvent (a) or (c). If in the reaction system during the reaction is water, ferrimagnet derivative (1), reacting with water, decomposes. Thus, it is preferable to replace the air in the reaction system, namely in the reaction flask, an inert gas such as nitrogen. In addition, it is preferable that the solvent (a) or (c) and boron halide (2) did not contain water. Method of drying solvent (a) or (c) and boron halide (2) is not particularly limited.

The reaction temperature preferably is in the range between 30oC and the boiling point of the solvent, inclusive, more preferably between 30oC and 200oC and SUP>C is not preferred because the reaction proceeds too slowly to effectively produce compounds (foradil)borane. On the other hand, when the reaction temperature exceeds the boiling point of the solvent, it becomes difficult to control the reaction.

The duration of reaction can be set arbitrarily to complete the reaction depending on the reaction temperature, the combination ferrimagnetic derivative (1) and boron halide (2), quantities used, and so on, the Pressure of reaction is not particularly limited and the reaction may proceed at normal (ambient), reduced or increased pressure.

The reaction solution containing the compound (foradil)borane expressed by the above General formula (3) can be obtained by the interaction of ferril magnesium derivative (1) with the boron halide (2) in accordance with the above-described method. When the reaction solution obtained using the solvent (a), the reaction solution is added to the solvent (b), while diethyl ether and/or tetrahydrofuran is distilled off from the reaction solution. When the reaction solution obtained using rastvorityelya (c), diethyl ether and/or tetr the>/BR>MgXaXb...

where Xais a chlorine atom, a bromine atom or an iodine atom, and Xbis a fluorine atom, chlorine atom, bromine atom or iodine atom, is obtained as a by-product along with the connection (foradil)borane and dissolved in the reaction solution.

The amount of solvent (b) subject to the above reaction solution is not particularly limited and can be used any number until the connection (foradil)borane is completely dissolved in it, in other words until the connection (foradil) borane can be obtained in the form of a solution after diethyl ether and/or tetrahydrofuran was distilled from a mixture solvent (b) and reaction solution.

The method of addition, the reaction solution obtained with the use of solvent (a), the solvent (b) is not particularly limited. However, preferably dropwise to the above reaction solution continuously or sequentially to the solvent (b), heated to 80oC or higher. Note that the temperature of the reaction solution is not particularly limited, while it is below the boiling point of diethyl ether or tetrahydrofuran.

The magnesium halide obtained is tetrahydrofuran, but not soluble in other solvents (namely the previously mentioned ether solvent and hydrocarbon solvent). In other words, the magnesium halide and the compound (foradil)borane dissolved in other solvents with different solubility. So, when adding the reaction solution to the solvent (b), heated to 80oC or higher, diethyl ether and/or tetrahydrofuran quickly boiled. Then the resulting mixture is not only distills diethyl ether and/or tetrahydrofuran, but it also precipitates and falls to the halide of magnesium. The halide of magnesium precipitates and falls in a form that is relatively easy to filter. Therefore, the magnesium halide produced as a by-product can be separated and removed from the mixture obtained after the distillation of diethyl ether and/or tetrahydrofuran. However, the separation and removal of the magnesium halide is not limited to filtering.

Method (regulation) distillation of diethyl ether and/or tetrahydrofuran not particularly limited. However, for the above mentioned reason, it is preferable to repel diethyl ether and/or tetrahydrofuran as quickly as possible. Thus, the most preferred method of distillation is holding thoroughy hand, when the distillation of diethyl ether and/or tetrahydrofuran from the reaction solution, obtained using the solvent (c), the reaction solution is heated to 80oC or above as soon as possible. Diethyl ether and/or tetrahydrofuran is distilled over under normal, reduced or increased pressure. It is preferable to conduct the above-described addition and distillation in an atmosphere of inert gas, such as nitrogen.

In accordance with the above described method it was possible to obtain compound (foradil)borane expressed by the above General formula (3) (hereinafter called compound (foradil)borane (3)), in other words, the connection (foradil)borane (3), such as Tris(foradil)borane and bis (foradil)boryl halide, which separates and removes the magnesium halide produced as a by-product. Connection (foradil)borane (3), in particular Tris(foradil)borane, suitable, for example, as socializaton promotion activity of the metallocene catalyst (polymerization catalyst). In addition, when ferril magnesium derivative (1) is panafcortelone bromide, compound (pentafluorophenyl)borane, such as Tris(pentafluorophenyl)borane and bis(pentatone is, you can now to get a simple manner at low cost. If the connection (foradil)borane (3) remains diethyl ether or tetrahydrofuran, the potency of the compound (foradil)borane (3) as socializaton deteriorating. For this reason, preferably, repel virtually all amount of diethyl ether or tetrahydrofuran.

Next, the reaction solution containing the derived tetrakis (foradil)borate expressed by the above General formula (5) (hereinafter called derived tetrakis(foradil)borate (5)), get in the interaction of the above-mentioned compounds (foradil)borane (3), from which is separated and removed a magnesium halide, with ferrimagnetism derivative (4). Preferably, this ferrimagnet derivative (4) was in the form of a solution by being dissolved in diethyl ether and/or tetrahydrofuran, or a solvent (d) (hereinafter, the resulting solution is called a solution of the magnesium derivative (4)). Concentration ferrimagnetic derivative (4) in the solution is not particularly limited.

The molar ratio of compounds (foradil)borane (3) and ferrimagnetic derivative (4) (compound (foradil)borane (3)/ferrimagnet proizvodnog value, equal to 1.0. When the molar ratio is much greater than or less than 1.0, derived tetrakis(foradil)borate (5) cannot be obtained efficiently.

A method of mixing a solution of the compound (foradil)borane (3) with a solution of magnesium derivative (4) is not particularly limited. Both types of solutions can be mixed simultaneously, or one of the solutions can dropwise to another continuously or sequentially.

The temperature of the mixed solution of the compound (foradil)borane (3) with a solution of magnesium derivative (4) is not particularly limited. However, it is preferable to set the temperature of the mixture in the range between -20oC and the boiling point of the solvent, inclusive, more preferably in the range between -20oC and 100oC and most preferably in the range between the 20oC and 70oC. Since the reaction is easier to control when mixing both types of solutions in the above ranges of temperature, the setting temperature of the mixture below -20oC does not result in significant effects and therefore disadvantageous for industrial use in comparison with a case in which the temperature of the mixture is set in the above range of temperatures. On the other hand, when tempera">

When a solution of compounds (foradil)borane (3) and a solution of magnesium derivative (4) mixed together and stirred, the resulting solution of the compound (foradil)borane (3) and magnesium derivative (4) begin to react with each other. If the reaction in the reaction system is water, ferril magnesium derivative (4) by reacting with water, decomposes. Thus, it is preferable that the above-mentioned reaction proceeded in an atmosphere of inert gas, such as nitrogen. In addition, preferably by mixing with each other both types of solutions to replace the air in the reaction system, namely in the reaction flask, an inert gas such as nitrogen. The method of drying the magnesium derivative (4) is not particularly limited.

The reaction temperature is set so that it ranged between 30oC and the boiling point of the solvent, inclusive, more preferably in the range between the 50oC and the boiling point of the solvent, inclusive, and most preferably in the range between 60oC and the boiling point of the solvent, inclusive. Setting the reaction temperature below 30oC is not preferred because the reaction proceeds when the reaction temperature exceeds the boiling point of the solvent, it becomes difficult to control the reaction.

The duration of reaction can be set arbitrarily to complete the reaction depending on the reaction temperature, the combination of compounds (foradil)borane (3) and FERRYL magnesium derivative (4), quantities used, and so on, the Pressure of reaction is not particularly limited and the reaction may proceed at normal (ambient), reduced or increased pressure.

In the above-described method produces a solution containing a derivative tetrakis(foradil)borate (5). When the connection (foradil)borane (3) is a bis(foradil)boryl halide, magnesium halide, expressed by the General formula (C):

MgXbXc...

where Xbis a fluorine atom, chlorine atom, bromine atom or iodine atom, and Xcis a chlorine atom, a bromine atom or an iodine atom, is obtained as a by-product, along with the derived tetrakis(foradil)borate (5) and is dissolved in the reaction solution. So, in order to separate and remove the magnesium halide from the reaction solution, the reaction solution is distilled diethyl ether and/or tetrahydrofuran, if circumstances so require.

In R. magnesium, obtained as a by-product is separated and removed. Derived tetrakis(foradil)borate (5) is a relatively stable compound and according to the above method derived tetrakis(foradil)borate (5) can be isolated from the reaction solution in the form of crystals or solution.

In other words, according to the above method after communication connection (foradil)borane (3) and FERRYL magnesium derivative (4) in the solvent (d) diethyl ether and/or tetrahydrofuran is distilled off from the reaction system. For example, when compound (foradil)borane (3) is dis(foradil)boil a halide, a magnesium halide produced as a by-product along with the derived tetrakis(foradil)borate (5), falls out of the reaction system and deposited. In short, the magnesium halide produced as a by-product can be separated and removed. As a result, it was possible to obtain a derived tetrakis(foradil)borate (5), from which is obtained as a by-product of a magnesium halide can be separated and removed in a simple manner at low cost. In addition, the thus obtained derivative tetrakis(foradil)borate (5) is atmono highlight of the reaction solution in the form of crystals or solution. When the connection (foradil)borane (3) is a compound Tris (foradil)borane derived tetrakis(foradil)borate (5) can be isolated from the reaction solution in the form of crystals or solution.

Next will be explained the method of deriving tetrakis(foradil)borate expressed above General formula (10) (hereinafter called derived tetrakis(foradil)borate (10)) using aryl fluoride (6) as the source connection.

Examples of aelfthryth (6) are: pentafluorobenzoyl, 1,2,3,5 - tetrafluorobenzene, 1,2,4,5-tetrafluorobenzene, 1,2,4-triftorbyenzola, 1,3,5-triftorbyenzola, 1,3-differental, 2,3,5,6-tetrachordal, 2,3,4,6-tetrachordal, 2,3,5-triptorelin, 2,4,6 - triptorelin, 2,4-dipertua, 2,3,5,6-teratornis, 2,3,4,6-teratornis, 2,4,5-triparanol, 2,4,6-triparanol, 2,4-differenital, 3,5-differenital etc.

Halogen-substituted hydrocarbon (7) is a compound in which the substituting group, denoted as Rois a hydrocarbon group, and the replacement group, denoted as Xais a chlorine atom, a bromine atom or an iodine atom. Examples of the hydrocarbon group include: aryl group, an alkyl group with direct CPA with a straight chain, branched chain or cyclic Alchemilla group containing 2-12 carbon atoms and so on, the Hydrocarbon group may further include a functional group that remains inactive in the reactions in the present invention. Examples of such functional groups are: methoxy group, methylthiourea, N,N-dimethylaminopropan, risograph, p-anthrope, trimethylsilyl group, tert-butyldimethylsilyloxy, triptorelin group, etc.

Examples of halogen-substituted hydrocarbon (7) are: methyl chloride, methyl bromide, methyl iodide, ethyl chloride, bromide, ethyl iodide, ethyl chloride, n-propyl, methyl n-propyl, iodide, n-propyl, chloride, ISO-propyl, methyl ISO-propyl, iodide, ISO-propyl, chloride n-butyl, methyl n-butyl, iodide, n-butyl, chloride, ISO-butyl, methyl ISO-butyl, iodide, ISO-butyl, chloride, sec-butyl, methyl sec-butyl, iodide, sec-butyl, chloride, tert-butyl, methyl tert-butyl, iodide, tert-butyl, hexyl chloride, hexyl bromide, iodide, hexyl, cyclohexyl chloride, methyl-cyclohexyl, cyclohexyl iodide, allyl chloride, allyl bromide, allyl iodide, chlorobenzene, bromans what about the hydrocarbon (7).

The ratio of the halogen-substituted hydrocarbon (7) and halftoned (6) is not particularly limited. However, this ratio is preferably 0.5 or more for the equivalent. More preferably the ratio is in the range between 0.5 and 3.0 on equivalent and most preferably between 0.8 and 1.5 for the equivalent. When the ratio of the halogen-substituted hydrocarbon (7) is less than 0.5 equivalent value, but there are too many unreacted halftoned (6) in order to effectively get ferrimagnet derivative (8).

For further promotion of the reaction it is preferable that the magnesium was in the form with a large surface area, such as, for example, powders, granules and thin slices (chips). The ratio of magnesium and halftoned (6) is not particularly limited. However, this ratio is preferably 0.5 or more for the equivalent. More preferably the ratio is in the range between 0.5 and 3.0 on equivalent and most preferably between 0.8 and 1.5 for the equivalent. When the ratio of magnesium is less than 0.5 equivalent value, but there are too many unreacted aryl fluoride (6) in order ferrimagnet derivative (8) was obtained Realem (a) is not particularly limited. Examples of order of mixing are:

1) halftoned (6), halogensubstituted hydrocarbon (7) and magnesium mixed with the solvent (a) almost simultaneously;

2) halftoned (6) and magnesium mixed with the solvent (a), then add halogensubstituted hydrocarbon (7);

3) halftoned (6) is first mixed with the solvent (a), and then halogensubstituted hydrocarbon (7) and magnesium mixed with the resulting solution almost simultaneously;

4) magnesium is first mixed with the solvent (a), and then halftoned (6) and halogensubstituted hydrocarbon (7) is mixed with the resulting solution almost simultaneously,

5) magnesium, halftoned (6) and halogensubstituted hydrocarbon (7) is mixed with the solvent (a) sequentially in this order;

6) halftoned (6) and halogensubstituted hydrocarbon (7) is mixed with the solvent (a), then add the magnesium.

All of the examples about the most preferred is a mixture of halftoned (6) and magnesium with the solvent (a), followed by the addition of halogen-substituted hydrocarbons (7). However, preferably continuous or sequential addition, since the reaction is easier to control. The method of addition is not particularly limited to the dilute solvent (a) before precapitalism.

The temperature of the mixture at which halftoned (6) and/or halogen-substituted hydrocarbon (7) is mixed with the solvent (a) is not particularly limited. However, when the mixture of halogen-substituted hydrocarbon (7) with the solvent (a) the preferred temperature of the mixture is in the range between -20oC and the boiling point of the solvent, inclusive. It is more preferable to set the temperature of the mixture in the range between -20oC and 100oC and most preferably in the range between the 20oC and 70oC. Because when mixed halogen-substituted hydrocarbon (7) with the solvent (a) within the specified limits of temperature, the reaction is easier to control. Establishing a mixing temperature below -20oC does not bring significant effects and therefore disadvantageous for industrial use compared with the case where the temperature of the mixture is within the specified limits of temperature. On the other hand, when the temperature of the mixture exceeds the boiling point of the solvent, it becomes difficult to control the reaction. For industrial use, the temperature of mixing is easy to install in the range between -20oC and the boiling point of the solvent, inclusive.

Halftoned (6), g is ω above nonaqueous solvent (a) and stirring. During the reaction the magnesium gradually dissolves in the solvent (a). If the reaction in the reaction system is water obtained ferrimagnet derivative (8) by reacting with water, decomposes. For this reason, it is preferable that the reaction proceeded in an atmosphere of inert gas, such as nitrogen. It is also preferable to replace the air in the reaction system, namely in the reaction flask, an inert gas such as nitrogen. In addition, it is preferable that the solvent (a), halftoned (6) and halogensubstituted hydrocarbon (7) did not contain water, and the drying halftoned (6), halogensubstituted hydrocarbon (7) and solvent (a) is not particularly limited.

The reaction temperature is preferably set in the range between 30oC and the boiling point of the solvent, inclusive. It is more preferable to set the reaction temperature in the range between 30oC and 200oC and most preferably in the range between 30oC and 70oC. Setting the reaction temperature below 30oC is not preferred because the reaction proceeds too slowly to effectively produce ferrimagnetic derivative (8). On the other hand, when the temperature of the reaction dilnot reactions can be set arbitrarily to complete the reaction depending on the reaction temperature, the combination of halftoned (6) and halogensubstituted hydrocarbon (7), quantities used, and so on, the Pressure of reaction is not particularly limited and the reaction may proceed at normal (ambient), reduced or increased pressure.

In the above method is obtained ferrimagnet derivative (8). In other words, the result is a solution ferrimagnetic derivative (8). In addition, as a by-product obtained hydrocarbon, expressed by the General formula (D):

RoH...

where Rois a hydrocarbon group. If circumstances require, the hydrocarbon can be removed from ferrimagnetic derivative (8) and the method of removal is not particularly limited.

Then, when interacting ferrimagnetic derivative (8) obtained by the above method, the boron halide (2) in situ obtained compound (foradil)borane expressed by the above General formula (9) (hereinafter called compound (foradil)borane (9)). The molar ratio ferrimagnetic derivative (8) and boron halide (2) is not particularly limited, but preferred above precautionary limits.

A method of mixing a solution of fluorine is the solution at once or dropwise to the solution continuously or sequentially. The boron halide (2) was added dropwise to the solution directly or diluted with solvent (a) before precapitalism.

The temperature of the mixture and the reaction temperature by mixing ferrimagnetic derivative (8) with the boron halide (2) is not particularly limited. However, it is preferable to set the temperature of the mixture and the reaction temperature in the above example. The duration of reaction can be set arbitrarily to complete the reaction depending on the reaction temperature, the combination ferrimagnetic derivative (8) and boron halide (2), quantities used, and so on, the Pressure of reaction is not particularly limited, and the reaction may proceed at normal (ambient) reduced or increased pressure.

In the above-described method produces a solution containing compound (foradil)borane (9). Then, the magnesium halide produced as a by-product is separated and removed from the reaction system when adding the reaction solution to the solvent (b), while diethyl ether and/or tetrahydrofuran is distilled off from the reaction solution, after which it should filter. As a result, it was possible to obtain soedinenii halide, of which separates and removes the magnesium halide expressed above General formula (B).

Then, when interacting compounds (foradil)borane (9), from which it is separated and removed a magnesium halide, with ferrimagnetism derivative (4) obtain the reaction solution containing the derived tetrakis(foradil) borate (10). When the connection (foradil)borane (9) is a bis(foradil)boryl halide, magnesium halide produced as a by-product, along with the derived tetrakis(foradil)borate (10) and expressed the above General formula (C), is dissolved in the reaction solution. So, for separation and removal of the magnesium halide from the reaction solution is distilled diethyl ether and/or tetrahydrofuran. On the other hand, when the compound (foradil)borane (9) is a Tris(foradil)borane, diethyl ether and/or tetrahydrofuran is distilled off from the reaction solution, if circumstances so require.

According to the above method derived tetrakis(foradil)borate (10), from which the magnesium halide produced as a by-product is separated and removed, can be obtained in a simple manner at low cost, using aryl fluoride (6) vtorri)borate, expressed in the above General formula (11) and derived tetrakis(foradil)borate expressed above General formula (13).

The method of deriving tetrakis(foradil)borate expressed above General formula (11), in the present invention is a method of interaction halftoned (6), halogensubstituted hydrocarbon (7) and magnesium in an ether solvent (e), or a mixed solvent consisting of ether solvent (e) and the hydrocarbon solvent, to obtain ferrimagnetic derivative (8) and the subsequent interaction obtained ferrimagnetic derivative (8) with the boron halide (2). The ratio of the halogen-substituted hydrocarbon (7) and aryl fluoride (6) and the ratio of magnesium and aryl fluoride (6) is not particularly limited. However, preferred above precautionary limits.

The method of deriving tetrakis(foradil)borate expressed above General formula (13), in the present invention is a method in which after receiving ferrimagnetic derivative (8), ferrimagnetic derivative (8) and Tris(foradil)borane expressed above General formula (12) (hereinafter nativeamerican, while it is a liquid compound that is inactive in the reactions in the present invention, and in which are dissolved halftoned (6), halogensubstituted hydrocarbon (7), ferrimagnetic derivative (8) as intermediate, derived tetrakis(foradil)borate as the target product and a boron halide (2) or Tris(foradil)borate (12). Examples of the ether solvent (e) include diethyl ether, tetrahydrofuran and the above-mentioned ether solvents. You can effectively use one member or a mixture of two or more members selected from these examples. From all these examples, preferred are diethyl ether and tetrahydrofuran as the reaction proceeds faster. When using a mixture of two or more members selected from these examples, it is preferable that the mixture consisted of either diethyl ether or tetrahydrofuran.

The amount of solvent (e) is not particularly limited. For example, preferably a number, in which the concentration obtained ferrimagnetic derivative (8) is in the range between 0.1 and 80 weight percent. The hydrocarbon solvent is not particularly limited as long as it is a liquid compound that osteo solvent (e) and the hydrocarbon solvent is not particularly limited, while these solvents are mixed in a homogeneous mix the mixture. However, preferably, this ratio ranged between 1: 0 and 1:10 by volume. The number of mixed non-aqueous solvent is not particularly limited. For example, preferably a number, in which the concentration obtained ferrimagnetic derivative (8) is in the range between 0.1 and 80 weight percent.

The order of mixing halftoned (6), halogensubstituted hydrocarbon (7) and magnesium with ether solvent (e), or a mixed solvent consisting of ether solvent (e) and the hydrocarbon solvent (hereinafter called together just solvent (e)), is not particularly limited. For example, here is also applicable orders of mixing methods and mixing halftoned (6), halogensubstituted hydrocarbon (7) and magnesium with the solvent (a). Reaction conditions such as temperature, mixing, reaction temperature and duration of reaction when mixing halftoned (6) and/or halogen-substituted hydrocarbon (7) with the solvent (e) is not particularly limited. For example, here is also applicable reaction conditions, such as temperature, mixing, reaction temperature and duration of reaction, importresult the above method is obtained ferrimagnet derivative (8). In other words, the result is a solution ferrimagnetic derivative (8). In addition, the result is a hydrocarbon, expressed by the above General formula (D).

Then, when interacting ferrimagnetic derivative (8) obtained by the above method, the boron halide (2) in situ obtained derived tetrakis(foradil)borate expressed by the above General formula (11) (hereinafter called derived tetrakis(foradil)borate (11)). In addition, the interaction ferrimagnetic derivative (8) with Tris (foradil)borane (12) obtained in situ derived tetrakis (foradil)borate expressed by the above General formula (13) (hereinafter called derived tetrakis(foradil)borate (13)).

The ratio of boron halide (2) and ferrimagnetic derivative (8) is not particularly limited. However, preferably, this ratio was close to theoretical value equal to 0.25 equivalent value. When the ratio is much larger or smaller than 0.25 equivalent value derived tetrakis(foradil)borate (11) cannot be obtained efficiently.

The method of mixing the solution ferrimagnetic derivative (8) and boron halide (2) is not particularly limited. the nutrient. The boron halide (2) can directly be mixed or diluted with a solvent (e) before mixing.

The temperature of the mixture when the mixture solution ferrimagnetic derivative (8) and boron halide (2) is not particularly limited. However, it is preferable that the temperature of the mixture was set in the range between -20oC and the boiling point of the solvent, more preferably in the range between -20oC and 100oC and most preferably in the range between the 20oC and 70oC. Because by mixing the above-mentioned two compounds within the specified limits of temperature, the reaction is easier to control, which makes it possible to derive tetrakis (foradil)borate (11) more effectively in a simple way. Establishing a mixing temperature below -20oC does not bring significant effects and therefore disadvantageous for industrial use in comparison with a case in which the temperature of mixing is installed in the specified temperature limits. On the other hand, when the temperature of the mixture exceeds the boiling point of the solvent, it becomes difficult to control the reaction.

By mixing and stirring of the solution ferrimagnetic production is Rog with each other in the resulting solution. If the reaction in the reaction system is water obtained ferrimagnet derivative (8) by reacting with water, decomposes. For this reason, it is preferable that the reaction proceeded in an atmosphere of inert gas, such as nitrogen. It is also preferable to replace the air in the reaction system, namely in the reaction flask, an inert gas such as nitrogen. In addition, it is preferable that the boron halide (2) did not contain water.

The reaction temperature is preferably set in the range between 30oC and the boiling point of the solvent, inclusive. It is more preferable to set the reaction temperature in the range between the 50oC and the boiling point of the solvent, inclusive, and most preferably in the range between 60oC and the boiling point of the solvent, inclusive. Because when the reaction within the specified limits of temperature, the reaction is easier to control, which makes it possible to derive tetrakis (foradil)borate (11) more effectively in a simple way. Setting the reaction temperature below 30oC is not preferred because the reaction proceeds too slowly to effectively obtain PR is singing solvent, it becomes difficult to control the reaction.

The duration of reaction can be set arbitrarily to complete the reaction depending on the reaction temperature, the combination ferril magnesium derivative (8) and boron halide (2), quantities used, and so on, the Pressure of reaction is not particularly limited, and the reaction may proceed at normal (ambient), reduced or increased pressure.

In the above method is obtained derived tetrakis(foradil)borate (11). In addition, as a by-product we get the halide of magnesium, expressed by the above General formula (In). The magnesium halide can be removed from the derived tetrakis(foradil)borate (11), if circumstances require, and the method of removal is not particularly limited.

Tris(ferril borane) (12) is a compound in which each of the substituting groups, denoted as R11-R25is a hydrogen atom, a hydrocarbon group or alkoxygroup, while at least one of R11-R25is a fluorine atom. Examples of the hydrocarbon group and alkoxygroup are the above examples of the hydrocarbon group and alkoxygroup, slopestyle is a connection, in which at least one of the substituting groups, denoted as R11-R15at least one of the substituting groups, denoted as R16-R20and at least one of the substituting groups, denoted as R21-R25is a fluorine atom, respectively, in other words, the connection in which three aryl groups associated with boron, are fluorinated.

Examples of Tris(foradil)borane (12) are: Tris(pentafluorophenyl)borane, Tris(2,3,4,6 - tetrafluorophenyl)borate, Tris(2,3,5,6-tetrafluorophenyl)borate, Tris(2,3,5-tryptophanyl)borane, Tris(2,4,6-tryptophanyl)borane, Tris(1,3-differenl)borane, Tris(2,3,5,6-titrator-4 - were)borane, Tris(2,3,4,6-titrator-5-were)borane, Tris(2,4,5-Cryptor-6-were)borane, Tris(2,3,6-Cryptor - 4-were)borane, Tris(2,4,6-Cryptor-3-were)borane, Tris(2,6-debtor-3-were)borane, Tris(2,4-debtor-5 - were)borane, Tris(3,5-debtor-2-were)borane, Tris(4 - methoxy-2,3,5,6-tetrafluorophenyl)borane, Tris(3-methoxy-2,4,5, 6-tetrafluorophenyl)borane, Tris(2-methoxy-3,5,6-tetrafluorophenyl) borane, Tris(3-methoxy-2,5,6-tetrafluorophenyl)borane, Tris(3 - methoxy-2,4,6-tetrafluorophenyl)borane, Tris(2-methoxy-3,5 - tetrafluorophenyl)borane, Tris(3-methoxy-2,6-tetrafluorophenyl) borane, Tris(3-labels the. what if circumstances so require, you can use more than one form of Tris(foradil)Baranov (12).

The ratio of Tris(foradil)borane (12) and ferrimagnetic derivative (8) is not particularly limited. However, preferably, this ratio was close to theoretical ratio of 1.0 equivalent value. When the ratio is much greater than or less than 1.0 equivalent value derived tetrakis(foradil) borate (13) cannot be obtained efficiently.

The method of mixing the solution ferril magnesium derivative (8) and Tris(foradil)borane (12) is not particularly limited. Tris (foradil)borane (12) can be added to the solution at once or dropwise to the solution continuously or sequentially. Tris (foradil)borane (12) can be directly mixed or diluted with a solvent (e) before mixing.

The temperature of the mixture when the mixture solution ferrimagnetic derivative (8) and Tris(foradil)borane (12) is not particularly limited. However, it is preferable that the temperature of the mixture was set in the range between -20oC and the boiling point of the solvent, inclusive, more preferably in the range between - 20oC and 100oC and most preferably in before the temperature of the reaction is easier to control, in result, it becomes possible to derive tetrakis(foradil)borate (11) more effectively in a simple way. Establishing a mixing temperature below -20oC does not bring significant effects and therefore disadvantageous for industrial use in comparison with a case in which the temperature of mixing is installed in the specified temperature limits. On the other hand, when the temperature of the mixture exceeds the boiling point of the solvent, it becomes difficult to control the reaction.

By mixing and stirring of the solution ferrimagnetic derivative (8) and Tris(foradil)borane (12), ferrimagnetic derivative (8) and Tris(foradil)borane (12) begin to interact with each other in the resulting solution. Preferably, the reaction proceeded in an atmosphere of inert gas, such as nitrogen. Also, it is preferable to replace the air in the reaction system, namely in the reaction flask by mixing the two compounds, inert gas such as nitrogen. In addition, preferably, Tris(foradil)borane (12) did not contain water, and the drying Tris(foradil)borane (12) is not particularly limited.

The reaction temperature is preferably set in the range between 30AI in the range between the 50oC and the boiling point of the solvent, inclusive, and most preferably in the range between 60oC and the boiling point of the solvent, inclusive. Because when the reaction proceeds within the specified limits of temperature, the reaction is easier to control, which makes it possible to derive tetrakis(foradil)borate (13) more effectively in a simple way. Setting the reaction temperature below 30oC is not preferred because the reaction proceeds too slowly to effectively deriving tetrakis(foradil)borate (13). On the other hand, when the reaction temperature exceeds the boiling point of the solvent, it becomes difficult to control the reaction.

The duration of reaction can be set arbitrarily to complete the reaction depending on the reaction temperature, the combination ferrimagnetic derivative (8) and Tris(foradil)borane (12), quantities used, and so on, the Pressure of reaction is not particularly limited and the reaction may proceed at normal (ambient), reduced or increased pressure.

In the above method is obtained derived tetrakis(foradil)borate (13). Crainey least one of the four porarily groups associated with boron differs from the structure of the rest.

As was explained, the method of deriving tetrakis(foradil)borate (11) of the present invention is a method of interaction halftoned (6), halogenosilanes hydrocarbon (7), and magnesium in a solvent (e) to obtain ferrimagnetic derivative (8) and the subsequent interaction obtained ferrimagnetic derivative (8) with the boron halide (2).

In addition, as was explained, the method of deriving tetrakis(foradil) borate (13) of the present invention is a method in which after receiving ferrimagnetic derivative (8), ferrimagnetic derivative (8) interacts with Tris(foradil)borane (12).

According to these methods, the reaction proceeds in fact at one stage. In addition, according to the above methods derived tetrakis(foradil)borate (11) and (13) can be obtained with high yields and selectivity. Consequently, derivatives of tetrakis(foradil)borate (11) and (13) can now be obtained in a simple way and at low cost. Derivatives of tetrakis(foradil)borate (11) and (13) may be useful as cationic complex polymerization. Note that the derivatives of tetrakis(foradil)borate (11) and (13) are relatively stable compounds and can be separated from the reaction system in the form of crystals or solution, as circumstances require, and the method of allocation is not particularly limited.

Further, the present invention will be explained in detail by examples. However, the present invention is not limited to the following description.

EXAMPLE 1

In a reaction vessel equipped with a thermometer, dropping funnel, stirrer, the input of nitrogen and reflux condenser, the air was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 2,874 g (0,0203 mol) of titlefirst boron TRIFLUORIDE, which is a boron halide (2), and 40 ml of diethyl ether solvent (a). In addition, the addition funnel was placed 30 ml of diethyl ether solution of magnesium derivative (1)) containing 0,0624 mol pentafluorophenyl magnesium bromide, employee ferrimagnetism derivative (1). The concentration of pentafluorophenyl magnesium bromide solution in diethyl ether is of 2.08 mol/l Molar ratio of pentafluorophenyl magnesium bromide and detragiache boron TRIFLUORIDE is 3.1.

Then to have etilovogo ether in a nitrogen atmosphere. The temperature of the contents at the beginning of the addition was 31oC (the temperature of the mixture) and in the course of the addition has risen to 36oC. Upon completion of addition the reaction solution was subjected to reaction (maturing) for 3 hours at 34oC (reaction temperature) with stirring. As a result, there was obtained a solution of crude Tris(pentafluorophenyl)borane in diethyl ether as compounds (foradil)borane (3).

Then in the distillation flask equipped with thermometer, dropping funnel, stirrer and refrigerator Liebig, was placed 300 ml of toluene serving as a solvent (b). The end of the output fridge Liebig opened, and the receiver is installed in a predetermined position. In addition, the addition funnel was placed a solution of crude Tris(pentafluorophenyl)borane in diethyl ether.

Then toluene was heated to 80oC under stirring, and then for 1 hour to bury the toluene solution of diethyl ether from a dropping funnel, maintaining toluene at 80oC. Distillation of diethyl ether at normal pressure started in parallel with precapitalism. Upon completion of the addition the contents (mixed substance) in the distillation flask was heated to 110oC so that titillatio to room temperature. Subsequently, the contents were filtered in a nitrogen atmosphere to separate fluoride, magnesium bromide, obtained as a by-product of Tris(pentafluorophenyl)borane. As a result, Tris(pentafluorophenyl) borane, which separated fluoride, magnesium bromide, obtained in the form of a solution in toluene (filtrate).

The yield of Tris(pentafluorophenyl)borane is defined when registering NMR19F. more Precisely, NMR19F registered in predetermined conditions using p-Tortolla as an internal standard reagent. Then, first, from the received NMR spectrum19F calculated value of the integral of a fluorine atom in p-portalware and the value of the integral of fluorine atoms in the ortho-positions of Tris(pentafluorophenyl)borane, and then, using the above two values of the integrals calculated the amount of Tris(pentafluorophenyl)borane. As a result, the determined reaction yield of Tris(pentafluorophenyl)borane was $ 81.8 mole percent when the purity of 93.2% in relation to the pentafluorophenyl magnesium bromide.

EXAMPLE 2

The air in the reaction vessel of the same type as used in example 1 was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 5,238 g (0,0369 the creators of diethyl ether, containing 0,1151 mol pentafluorophenyl magnesium bromide. The concentration of pentafluorophenyl magnesium bromide solution in diethyl ether is 2,30 mol/l Molar ratio of pentafluorophenyl magnesium bromide and detragiache boron TRIFLUORIDE is 3.1. Then to the specified content within 30 minutes under stirring was bury a solution of diethyl ether in a nitrogen atmosphere. The temperature of the contents at the beginning of the addition was 31oC during the addition has risen to 37oC. Upon completion of addition the reaction solution was subjected to reaction (maturing) for 3 hours at 35oC under stirring. As a result, there was obtained a solution of crude Tris(pentafluorophenyl)borane in diethyl ether.

Then 300 ml of cyclohexane, which serves as a solvent (b), was placed in a distillation flask of the same type as used in example 1. Also a solution of crude Tris(pentafluorophenyl)borane in diethyl ether was placed in an addition funnel. Then cyclohexane was heated to 70oC under stirring, and then for 1 hour to bury the cyclohexane solution of diethyl ether from the dropping funnel, while maintaining the cyclohexane at 70oC. Distillation of diethyl ether under normal the distillation flask was heated to 80oC so that diethyl ether was tognella almost completely.

After distillation of diethyl ether content was cooled to room temperature. The result of Tris(pentafluorophenyl)borane, which has separated is obtained as a by-product fluoride magnesium bromide was obtained in the form of a solution in cyclohexane in the same manner as in example 1. The reaction yield of Tris(pentafluorophenyl)borane, defined in the same manner as in example 1 totals 88.3 mol%, with the purity of 94.7 percent.

EXAMPLE 3

The air in the reaction vessel of the same type as used in example 1 was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 7,432 g (0,0520 mol) of titlefirst boron TRIFLUORIDE and 70 ml of diethyl ether. Then, in the addition funnel was placed 70 ml of diethyl ether containing 0,1129 mol pentafluorophenyl magnesium bromide. The concentration of pentafluorophenyl magnesium bromide solution in diethyl ether is of 2.26 mol/l Molar ratio of pentafluorophenyl magnesium bromide and detragiache boron TRIFLUORIDE is 2.2. Then to the specified content within 30 minutes under stirring was bury a solution of diethyl ether in the atmosphere azo the 36oC. Upon completion of addition the reaction solution was subjected to reaction (maturing) for 3 hours at 35oC under stirring. The result was obtained a solution of crude Tris(pentafluorophenyl) borane in diethyl ether.

Then 300 ml of xylene, which serves as a solvent (b), was placed in a distillation flask of the same type as used in example 1. Also a solution of crude Tris(pentafluorophenyl)borane in diethyl ether was placed in an addition funnel. Then the xylene was heated to 80oC under stirring, and then for 1 hour to bury the xylene solution of diethyl ether from a dropping funnel, maintaining xylene at 80oC. Distillation of diethyl ether at normal pressure started in parallel with precapitalism. Upon completion of the addition the contents (mixed substance) in the distillation flask was heated to 135oC so that diethyl ether was tognella almost completely.

After distillation of diethyl ether content was cooled to room temperature. As a result, Tris(pentafluorophenyl)borane, which has separated is obtained as a by-product fluoride magnesium bromide was obtained in the form of a solution in xylene in the same manner as in example 1. Reactio acenta with the purity 91,9%.

EXAMPLE 4

A solution of crude Tris(pentafluorophenyl)borane in diethyl ether obtained in the same manner as in example 3. Then 300 ml of n-octane, which serves as a solvent (b), was placed in a distillation flask of the same type as used in example 1. Also a solution of crude Tris(pentafluorophenyl)borane in diethyl ether was placed in an addition funnel. Then n-octane was heated to 80oC under stirring, and then for 1 hour to bury selalu solution of diethyl ether from the dropping funnel, while maintaining n-octane at 80oC. Distillation of diethyl ether at normal pressure started in parallel with precapitalism. Upon completion of the addition the contents (mixed substance) in the distillation flask was heated to 110oC so that diethyl ether was tognella almost completely. After distillation of diethyl ether content was cooled to room temperature. As a result, Tris(pentafluorophenyl)borane, which has separated is obtained as a by-product fluoride magnesium bromide was obtained in the form of a solution in n-octane in the same manner as in example 1. The reaction yield of Tris(pentafluorophenyl)borane, defined in the same manner as in example 1, is 92,0 mole%, with the purity of 92 is whether the nitrogen in a suitable way. Then the reaction vessel was placed 8,040 g (0,0569 mol) of titlefirst boron TRIFLUORIDE and 60 ml of diethyl ether. Then, in the addition funnel was placed 110 ml of diethyl ether containing 0,1707 mol pentafluorophenyl magnesium bromide. The concentration of pentafluorophenyl magnesium bromide solution in diethyl ether is 1.54 mol/l Molar ratio of pentafluorophenyl magnesium bromide and detragiache boron TRIFLUORIDE is 3.0. Then to the specified content within 1 hour with stirring was bury a solution of diethyl ether in a nitrogen atmosphere. The temperature of the contents at the beginning of the addition was 30oC during the addition is raised to the 32oC. Upon completion of addition the reaction solution was subjected to reaction (maturing) for 3 hours at 35oC under stirring. As a result, there was obtained a solution of crude Tris(pentafluorophenyl)borane in diethyl ether.

Then 250 ml dibutylamino ether solvent (b), was placed in a distillation flask of the same type as used in example 1. Also a solution of crude Tris(pentafluorophenyl)borane in diethyl ether was placed in an addition funnel. Then disutility ether was heated to 95oC when peremeshany, supporting disutility ether at 95oC. Distillation of diethyl ether at normal pressure started in parallel with precapitalism. Upon completion of the addition the contents (mixed substance) in the distillation flask was heated to 110oC so that diethyl ether was tognella almost completely.

After distillation of diethyl ether content was cooled to room temperature. As a result, Tris(pentafluorophenyl)borane, which has separated is obtained as a by-product fluoride magnesium bromide was obtained in the form of a solution in debutalbum ether in the same manner as in example 1. The reaction yield of Tris(pentafluorophenyl) borane, defined in the same manner as in example 1, is 86,8 mole%, with the purity of 89.8% of the.

EXAMPLE 6

The air in the reaction vessel of the same type as used in example 1 was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 2,695 g (0,0191 mol) of titlefirst boron TRIFLUORIDE, 20 ml of diethyl ether and 20 ml of toluene, both employees of the solvent (a). Then, in the addition funnel was placed 50 ml of a mixed solution of diethyl ether and toluene containing 0,0600 mol pentafluorophenyl magnesium bromide. Mixed sootnoshenie the sludge magnesium bromide in the mixed solution is 1.20 mol/L. In addition, the molar ratio of pentafluorophenyl magnesium bromide and detragiache boron TRIFLUORIDE is 3.1.

Then to the specified content within 1 hour with stirring was bury mixed solution in a nitrogen atmosphere. The temperature of the contents at the beginning of the addition was 28oC during the addition is raised to 35oC. Upon completion of addition the reaction solution was subjected to reaction (maturing) for 1 hour at 40oC under stirring. The result was obtained a solution of crude Tris(pentafluorophenyl)borane in a mixed solution of diethyl ether and toluene.

Then 100 ml of toluene serving as a solvent (b), was placed in a distillation flask of the same type as used in example 1. Also mixed solution of crude Tris(pentafluorophenyl)borane in diethyl ether and toluene was placed in an addition funnel. Then toluene was heated to 100oC under stirring, and then for 1 hour to bury the toluene mixed solution from the dropping funnel, while maintaining the toluene at 100oC. Distillation of diethyl ether at normal pressure started in parallel with precapitalism. Upon completion of the addition, the content in the distillation flask was heated Filologi ester content was cooled to room temperature. As a result, Tris(pentafluorophenyl)borane, which has separated is obtained as a by-product fluoride magnesium bromide was obtained in the form of a solution in toluene in the same manner as in example 1. The reaction yield of Tris(pentafluorophenyl)borane, defined in the same manner as in example 1, is 82,7 mole%, with the purity 91,0%.

EXAMPLE 7

The air in the reaction vessel of the same type as used in example 1 was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 16,95 g (0,120 mol) of titlefirst boron TRIFLUORIDE and 150 ml of diethyl ether. Then, in the addition funnel was placed 300 ml of diethyl ether containing 0,360 mol pentafluorophenyl magnesium bromide. The concentration of pentafluorophenyl magnesium bromide solution in diethyl ether is 1.20 mol/L. in Addition, the molar ratio of pentafluorophenyl magnesium bromide and detragiache boron TRIFLUORIDE is 3.0. Then to the specified content for 90 minutes with stirring was bury a solution of diethyl ether in a nitrogen atmosphere. The temperature of the contents at the beginning of the addition was 28oC during the addition has risen to 34oC. Upon completion of addition the reaction was obtained a solution of crude Tris (pentafluorophenyl)borane in diethyl ether.

Then 500 ml of toluene was placed in a distillation flask of the same type as used in example 1. Also a solution of crude Tris(pentafluorophenyl)borane in diethyl ether was placed in an addition funnel. Then toluene was heated to 35oC under stirring, and then for 90 minutes to bury the toluene solution of diethyl ether from a dropping funnel, maintaining toluene at 35oC. Distillation of diethyl ether at normal pressure started in parallel with precapitalism. Upon completion of the addition the temperature of the contents (mixed substances) in the distillation flask was gradually raised to 110oC, while began the distillation of diethyl ether at normal pressure, so that diethyl ether was tognella almost completely.

After distillation of diethyl ether content was cooled to room temperature. Subsequently, the contents were filtered in a nitrogen atmosphere so as to separate the Tris (pentafluorophenyl)borane from fluoride, magnesium bromide, obtained as a by-product along with Tris(pentafluorophenyl)borane. Although the inner wall of the distillation flask landed a significant amount of fluoride, bromide of magnesium, it has not caused any inconvenience during the filtration process. In the bromide of magnesium, was obtained in the form of a solution of toluene in the same manner as in example 1. The reaction yield of Tris(pentafluorophenyl)borane, defined in the same manner as in example 1, is of 75.0 mol%, with the purity of 85.5%.

EXAMPLE 8

Derived tetrakis(pentafluorophenyl)borate as derived tetrakis(foradil)borate (5) is obtained using a solution of Tris(pendaftaran)of borane in toluene obtained in example 1.

In a reaction vessel equipped with a thermometer, dropping funnel, stirrer, the input of nitrogen and refrigerator Liebig, the air was replaced with nitrogen in a suitable way. Then the reaction vessel was placed in 35 ml of diethyl ether solution of magnesium derivative (4)) containing 0,059 mol pentafluorophenyl magnesium bromide, the employee ferril magnesium derivative (4). The concentration of pentafluorophenyl magnesium bromide solution in diethyl ether is 1,67 mol/L. in Addition, the addition funnel was placed 116,0 g of a solution of Tris(pentafluorophenyl)borane in toluene obtained in example 1. The concentration of Tris(pentafluorophenyl)borane in toluene solution was 25.0 percent by weight, and in 116,0 g of toluene solution containing 0,057 mol of Tris(pentafluorophenyl)borane.

After distillation of diethyl ether content was cooled to room temperature. Then the salt crystals tetrakis(pentafluorophenyl)borate magnesium bromide fall out and are deposited as a derivative tetrakis(pentafluorophenyl)borate (5). Subsequently, the content was filtered to separate the crystals. As a result of 27.8 grams of salt is tetrakis(pentafluorophenyl)borate magnesium bromide with access 62,7 molar percent.

Next, the filtrate was heated under reduced pressure for distillation of toluene, and the amount of salt tetrakis(pentafluorophenyl)borate magnesium bromide contained in the residue was determined in the same manner as in example 1. Then it turned out that salt is tetrakis(pentafluorophenyl)borate magnesium bromide contained in the residue in an amount corresponding to the output of 2.0 mole percent. Thus, the total yield salts of tetrakis(pentafluorophenyl)borate magnesium bromide is 64,7 molar percent.

EXAMPLE 9

Derived tetrakis(pentafluorophenyl)b

In the reaction vessel of the same type as used in example 8, the air was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 20 ml of diethyl ether containing 0,008 mol pentafluorophenyl magnesium bromide. The concentration of pentafluorophenyl magnesium bromide solution in diethyl ether is 0,374 mol/L. in Addition, the addition funnel was placed 118.3 g of a solution of Tris(pentafluorophenyl)borane in cyclohexane obtained in example 2. The concentration of Tris (pentafluorophenyl)borane in solution of cyclohexane is 3,24 weight percent, and to 0.007 mol of Tris(pentafluorophenyl)borane contained in 118,03 g of the solution of cyclohexane.

Then to a solution of diethyl ether for 30 minutes at room temperature with stirring was bury solution of cyclohexane in a nitrogen atmosphere. Upon completion of the addition the contents of the reaction vessel was heated to 71oC to ensure that the contents were subjected to reaction (maturing) at that time as diethyl ether was distilled at normal pressure.

After distillation of diethyl ether content was cooled to room temperature. Then the content was divided into two layers. To be more precise, the contents are divided magni bromide. Then these two layers are separated from each other in the form of liquids. The result was obtained liquid salts of tetrakis(pentafluorophenyl)magnesium bromide. The reaction yield salts of tetrakis(pentafluorophenyl)magnesium bromide was determined by the same method as in example 1. Then, the determined reaction yield salts of tetrakis(pentafluorophenyl)magnesium bromide was 81,2 molar percent relative to the pentafluorophenyl magnesium bromide.

EXAMPLE 10

Derived tetrakis(pentafluorophenyl)borate obtained using a solution of Tris(pentafluorophenyl)borane in xylene obtained in example 3.

In the reaction vessel of the same type as used in example 8, the air was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 20 ml of diethyl ether containing 0,024 mol pentafluorophenyl magnesium bromide. The concentration of pentafluorophenyl magnesium bromide solution in diethyl ether is 1,22 mol/L. in Addition, the addition funnel was placed of 92.7 g of a solution of Tris(pentafluorophenyl)borane in xylene obtained in example 3. The concentration of Tris(pentafluorophenyl)borane in solution of xylene is 11,84 weight percent, and 0,021 mol of Tris(pentafluorophenyl)borane see what the atur under stirring was bury solution of xylene in nitrogen atmosphere. Upon completion of the addition the contents of the reaction vessel was heated to 130oC to ensure that the contents were subjected to reaction (maturing) at that time as diethyl ether was distilled at normal pressure.

After distillation of diethyl ether content was cooled to room temperature. Then the content was divided into two layers: the upper layer, consisting of xylene, and the lower layer consisting of liquid salts of tetrakis(pentafluorophenyl)magnesium bromide. Then these two layers are separated from each other in the form of liquids. The result was obtained liquid salts of tetrakis(pentafluorophenyl)magnesium bromide. The reaction yield salts of tetrakis(pentafluorophenyl)magnesium bromide defined in the same way as in example 1, made of 92.5 mole percent relative to the pentafluorophenyl magnesium bromide.

EXAMPLE 11

Derived tetrakis(pentafluorophenyl)borate obtained using a solution of Tris(pentafluorophenyl)borane in n-octane, obtained in example 4.

In the reaction vessel of the same type as used in example 8, the air was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 10 ml of diethyl ether containing of 0.017 mol pentaho is 68 mol/L. In addition, the addition funnel was placed with 85.4 g of a solution of Tris (pentafluorophenyl)borane in n-octane, obtained in example 4. The concentration of Tris(pentafluorophenyl)borane in solution n-octane is 8,89 weight percent, and 0.015 mol of Tris(pentafluorophenyl) borane contained in 85,4 g of a solution of n-octane.

Then to a solution of diethyl ether for 30 minutes at room temperature with stirring was bury a solution of n-octane in a nitrogen atmosphere. Upon completion of the addition the contents of the reaction vessel was heated to 110oC to ensure that the contents were subjected to reaction (maturing) at that time as diethyl ether was distilled at normal pressure.

After distillation of diethyl ether content was cooled to room temperature. Then the content was divided into two layers: the upper layer consisting of n-octane and the lower layer consisting of liquid salts of tetrakis(pentafluorophenyl)magnesium bromide. Then these two layers are separated from each other in the form of liquids. The result was obtained liquid salts of tetrakis(pentafluorophenyl)magnesium bromide. The reaction yield salts of tetrakis(pentafluorophenyl)magnesium bromide defined in the same way as in example 1, was 77,1 molar p is terphenyl)borate obtained using a solution of Tris(pentafluorophenyl)borane in debutalbum ether, obtained in example 5.

In the reaction vessel of the same type as used in example 8, the air was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 37 ml of diethyl ether containing 0,050 mol pentafluorophenyl magnesium bromide. The concentration of pentafluorophenyl magnesium bromide solution in diethyl ether is 1.34 mol/L. in Addition, the addition funnel was placed 139,0 g of a solution of Tris (pentafluorophenyl)borane in debutalbum ether obtained in example 5. The concentration of Tris(pentafluorophenyl)borane in solution dibutylamino ether amounts to 18.2 percent by weight, and 0,049 mol of Tris(pendaftaran)borane contained in 139,0 g of the solution dibutylamino ether.

Then to a solution of diethyl ether for 30 minutes at room temperature with stirring was bury solution dibutylamino ether in a nitrogen atmosphere. Upon completion of the addition the contents of the reaction vessel was heated to 137oC to ensure that the contents were subjected to reaction (maturing) at that time as diethyl ether was distilled at normal pressure.

After distillation of diethyl ether content was cooled to room temperature. Then the contents were divided into two the with(pentafluorophenyl)borate with debutalbum ether. Then these two layers are separated from each other in the form of liquids. As a result, there was obtained a liquid complex of tetrakis(pentafluorophenyl)borate with debutalbum ether. The reaction yield of the complex tetrakis(pentafluorophenyl) borate with debutalbum ether defined in the same way as in example 1, was 92,8 molar percent relative to the pentafluorophenyl magnesium bromide.

EXAMPLE 13

In a reaction vessel equipped with a thermometer, dropping funnel, stirrer, the input of nitrogen and reflux condenser, the air was replaced with nitrogen in a suitable way. Then the reaction vessel was placed of 1.027 g (0,042 mol) of magnesium, 6,810 g level (0.041 mol) of pentafluorobenzene serving aelfthryth (6), and 20 ml of diethyl ether solvent (e) (ether solvent (e)). In addition, the addition funnel was placed 4,945 g (0.040 mol) of isopropyl bromide, employee halogensubstituted hydrocarbon (7).

Then isopropyl bromide was bury to the above-mentioned content with stirring in a stream of nitrogen. Upon completion of the addition the resulting reaction solution was subjected to reaction (maturing) under stirring for 3 hours at 51,0oC (reaction temperature). As a result, as ferril magnetoactive output pentafluorophenyl magnesium bromide was determined at registration NMR19F. More precisely, after the reaction has taken part of the reaction solution and prepared the sample to be measured, mixing it with laterobasal in nitrogen atmosphere. In this case, the NMR19F was recorded in pre-determined conditions. Then, first, from the received NMR spectrum19F calculated value of the integral of the two fluorine atoms in the meta-positions of pentafluorobenzene and the value of the integral of the two fluorine atoms in the meta-positions pentafluorobenzene group, pentafluorophenyl magnesium bromide, and then, using the above two values of the integrals calculated the number of pentafluorophenyl magnesium bromide. Subsequently, the determined reaction output pentafluorophenyl magnesium bromide was $ 81.8 mole percent.

Then, the reaction vessel containing panafcortelone bromide, in a stream of nitrogen added there were 1,227 g (0,009 mol) of titlefirst boron TRIFLUORIDE, which is a boron halide (2), and mixed and mixed both compounds. The temperature of the contents during mixing (temperature of the mixture rose to 66,0oC, after which the resulting reaction solution was subjected to reaction under stirring for 2 hours. As a result, as derived tetrakis(pentafluorophenyl output derived tetrakis(pentafluorophenyl)borate was determined at registration NMR19F using p-Tortolla as an internal standard reagent. As a result, the reaction yield is derived tetrakis(pentafluorophenyl)borate amounted to 81.6 mole percent.

EXAMPLE 14

The air in the reaction vessel of the same type as in example 13 was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 2,040 g (0,084 mol) of magnesium, 13,577 g (of 0.081 mol) of pentafluorobenzene and 20 ml of diethyl ether. In addition, the addition funnel was placed 10,518 g (of 0.081 mol) of isopropyl bromide. Then isopropyl bromide was bury to the above-mentioned content with stirring in a stream of nitrogen. Upon completion of the addition the resulting reaction solution was subjected to reaction (maturing) under stirring for 3 hours at 63,0oC. as a result, was obtained pentafluorophenyl magnesium bromide in solution in diethyl ether. The reaction output pentafluorophenyl magnesium bromide defined in the same way as in example 13, was 80,0 molar percent.

Then, in the above-mentioned reaction vessel containing pentafluorophenyl magnesium bromide, in a stream of nitrogen added 2,248 g (to 0.016 mol) of titlefirst boron TRIFLUORIDE and shuffled and mixed both compounds. The temperature of the contents is rgli react under stirring for 2 hours. As a result, was derived tetrakis(pentafluorophenyl) borate in the form of a solution in diethyl ether. The reaction output derived tetrakis(pentafluorophenyl)borate, defined in the same way as in example 13, amounted to 79.6 molar percent.

EXAMPLE 15

The air in the reaction vessel of the same type as in example 13 was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 2,650 g (0,109 mol) of magnesium, 17,469 g (0.104 g mol) pentafluorobenzoyl, and 10 ml of diethyl ether and 10 ml of toluene, both employees of the solvent (e) (mixed solvent). In addition, the addition funnel was placed 14,185 g (0,109 mol) of isopropyl bromide. Then isopropyl bromide was bury to the above-mentioned content with stirring in a stream of nitrogen. Upon completion of the addition the resulting reaction solution was subjected to reaction (maturing) under stirring for 2.5 hours at 69,0oC. as a result, was obtained pentafluorophenyl magnesium bromide in the form of a mixed solution of diethyl ether and toluene. The reaction output pentafluorophenyl magnesium bromide defined in the same way as in example 13, amounted to 82.4 molar percent.

Then, in the above-mentioned reaction vessel containing pentaf is mixed both compounds. The temperature of the contents during mixing (temperature of the mixture rose to 78,0oC. Then, the reaction solution was subjected to reaction under stirring for 2 hours. As a result, was derived tetrakis(pentafluorophenyl)borate in the form of a mixed solution of diethyl ether and toluene. The reaction output derived tetrakis(pentafluorophenyl)borate, defined in the same way as in example 13, was 80.4 molar percent.

EXAMPLE 16

The air in the reaction vessel of the same type as in example 13 was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 2,025 g (0,083 mol) of magnesium, 13,198 g (0,079 mol) of pentafluorobenzene and 20 ml of tetrahydrofuran (THF) serving as a solvent (e) (ether solvent (e)). In addition, the addition funnel was placed 10,782 g (0,083 mol) of isopropyl bromide. Then isopropyl bromide was bury to the above-mentioned content with stirring in a stream of nitrogen. Upon completion of the addition the resulting reaction solution was subjected to reaction (maturing) under stirring for 2 hours at 57,0oC. as a result, was obtained pentafluorophenyl magnesium bromide in solution in THF. The reaction output pentafluorophenyl magnesium bromide above the reaction vessel, containing pentafluorophenyl magnesium bromide, in a stream of nitrogen added 2,005 g (0.014 mol) of the complex of boron TRIFLUORIDE with THF and mixed and mixed both compounds. The temperature of the contents during mixing (temperature of the mixture rose to 58,0oC. Then, the reaction solution was subjected to reaction under stirring for 2 hours. As a result, was derived tetrakis(pentafluorophenyl)borate in the form of a solution in THF. The reaction output derived tetrakis(pentafluorophenyl)borate, defined in the same way as in example 13, was 73,7 molar percent.

EXAMPLE 17

The air in the reaction vessel of the same type as in example 13 was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 2,008 g (0,082 mol) of magnesium, 13,529 g (of 0.081 mol) of pentafluorobenzene and 20 ml of diethyl ether. In addition, the addition funnel was placed 10,873 g (0,084 mol) of isopropyl bromide. Then isopropyl bromide was bury to the above-mentioned content with stirring in a stream of nitrogen. Upon completion of the addition the resulting reaction solution was subjected to reaction under stirring for 2 hours at 57,0oC. as a result, was obtained pentafluorophenyl magnesium bromide in solution in diety, the left 80,3 molar percent.

Then, in the above-mentioned reaction vessel containing pentafluorophenyl magnesium bromide, in a stream of nitrogen was added to the solution in amount 652,9 g (by 0.055 mol) obtained by dissolving Tris(pentafluorophenyl)borane, employee Tris(foradil)borane (12), cyclohexane (hydrocarbon solvent) so that the concentration of Tris(pentafluorophenyl)borane equal to 4, 31 weight percent, and mixed and mixed both compounds. The temperature of the contents during mixing (temperature offset) rose to 79,0oC. Then, the reaction solution was subjected to reaction under stirring for 2 hours. As a result, as derived tetrakis(pentafluorophenyl)borate was derived tetrakis(parafortan)borate (13) in the form of a mixed solution of diethyl ether and cyclohexane. The reaction output derived tetrakis(pentafluorophenyl)borate, defined in the same way as in example 13, was 87.7 molar percent relative to the pentafluorophenyl magnesium bromide.

EXAMPLE 18

The air in the reaction vessel of the same type as in example 13 was replaced with nitrogen in a suitable way. Then the reaction vessel was placed 1,503 g (0,062 mol) of magnesium, 9 the l) isopropyl bromide. Then isopropyl bromide was bury to the above-mentioned content with stirring in a stream of nitrogen. Upon completion of the addition the resulting reaction solution was subjected to reaction under stirring for 2 hours at 58,0oC. as a result, was obtained pentafluorophenyl magnesium bromide in solution in diethyl ether. The reaction output pentafluorophenyl magnesium bromide defined in the same way as in example 13, was 84,0 molar percent.

Then, in the above-mentioned reaction vessel containing pentafluorophenyl magnesium bromide, in a stream of nitrogen added br93.1 g level (0.041 mol) of a solution obtained by dissolving Tris(pentafluorophenyl) borane in toluene (hydrocarbon solvent) so that the concentration of Tris(pentafluorophenyl)borane was 22,82 weight percent, and mixed and mixed both compounds. The temperature of the contents during mixing (temperature of the mixture rose to 102.0oC. Then, the reaction solution was subjected to reaction under stirring for 2 hours. As a result, the derived tetrakis(pentafluorophenyl)borate was obtained in the form of a mixed solution of diethyl ether and toluene. The reaction output derived tetrakis(pentafluorophenyl)borate, is Agni bromide.

As described thus of the invention becomes clear that the above can be modified in many ways. Such changes should not be regarded as a departure from the spirit and scope of the invention and it is desirable that all such modifications, obvious to have experience in this field of technology, were included in the scope of the following claims.

EXAMPLE 19

The air in the reaction vessel similar to the vessel used in example 1 was replaced by nitrogen gas accordingly. Then 10 ml of diethyl ether as the ether solvent and 3,395 g /23,90 mmol/ titlefirst boron TRIFLUORIDE, which is a boron halide, are loaded into the reaction vessel. Next, 35 ml of diethyl ether containing 38,57 mmol pentafluorophenyl magnesium bromide, loaded into an addition funnel. The molar ratio of pentafluorophenyl magnesium bromide and detragiache boron TRIFLUORIDE is 1.6.

Then a solution of diethyl ether was added dropwise to the reaction vessel for more than half an hour at 25oC, under stirring in an atmosphere of nitrogen gas. The result is a solution of diethyl ether crude bis/pentafluorophenyl/borane.

Then Isopar E heated to 90oC, then a solution of diethyl ether crude bis/pentafluorophenyl/fluoride boryla was added dropwise to Isopar E within hours, while Isopar E is maintained at a temperature of 90oC. Begins distillation of diethyl ether. Upon completion of addition the reaction mixture is heated to 110oC. Diethyl ether Argonauts almost completely.

After distillation of diethyl ether contents cooled to room temperature and filtered in an atmosphere of nitrogen gas. Bis/pentafluorophenyl/fluoride barila separated from the fluoride, bromide of magnesium, which is produced as a by-product.

As a result, bis/pentafluorophenyl/fluoride barila get the connection /ferril/borane in solution /filtrate/ hydrocarbon dissolve/P> 1. The method of obtaining (foradil)borane General formula 3:

< / BR>
where each of R1- R5is a hydrogen atom, fluorine atom, alkyl group or alkoxygroup, and if at least one of R1- R5is a fluorine atom, Xinis a fluorine atom, bromine, chlorine or iodine;

n = 2 or 3,

including interaction ferrimagnetic derivative of General formula 1

< / BR>
where R1- R5described above;

Xandis a chlorine atom, bromine or iodine,

with the boron halide of General formula 2

< / BR>
where Xindescribed above

in solvent (a) containing diethyl ether and/or tetrahydrofuran, and the solvent (C) having a higher boiling point than diethyl ether and tetrahydrofuran, wherein the interaction ferrimagnetic derivative and boron halide is carried out in a solvent (a) and then adding the reaction solution to the solvent (b), heated to 80oC and above, followed by distillation of the solvent (a).

2. The method according to p. 1, characterized in that the solvent (b) has a boiling point of 60oC or higher.

3. The method according to p. 1, characterized in that the molar ethnosemantics in the range of 1.0 - 5,0.

4. The method according to p. 1, characterized in that the said ferrimagnetic derivative of General formula 1 and the above-mentioned boron halide of General formula 2, are mixed with each other at 80oC or below.

5. The method according to p. 1, characterized in that the said ferrimagnetic derivative of General formula 1 and the above-mentioned boron halide of General formula 2, interact with each other in the range between 30oC and the boiling point of the above-mentioned solvent (a) inclusive.

6. The method of obtaining (foradil)borane General formula 3

< / BR>
where each of R1- R5is a hydrogen atom, fluorine atom, alkyl group and alkoxygroup, and if at least one of R1- R5is a fluorine atom, Xinis an atom of fluorine, chlorine, bromine and iodine atom;

n = 2,

including interaction ferrimagnetic derived, expressed the General formula 1

< / BR>
where R1- R5described above;

Xandis a chlorine atom, bromine or iodine

with the boron halide of General formula 2

BXb3< / BR>
where Xbdescribed above

characterized in that the molar ratio ferrimagnetic derived 1 to the boron halide 2 o is the solvent (C), containing diethyl ether and/or tetrahydrofuran and the solvent having a higher boiling point than one of diethyl ether and/or tetrahydrofuran, and then distilled diethyl ether and/or tetrahydrofuran from the reaction solution.

7. The method according to p. 6, characterized in that the solvent (C) has a boiling point of 60oC or higher.

8. The method according to p. 6, characterized in that the molar ratio mentioned ferrimagnetic derived, expressed the General formula 1 to said boron halide expressed by General formula 2 (ferrimagnet derived/boron halide) is in the range of 1.0 to 5.0.

9. The method according to p. 6, characterized in that the said ferrimagnetic derivative expressed by General formula 1, and the above-mentioned boron halide expressed General formula 2, are mixed with each other at 80oWith or below.

10. The method according to p. 6, characterized in that the said ferrimagnet derivative of General formula 1 and the above-mentioned boron halide of General formula 2 interact with each other in the range between 30oC and the boiling point of the above-mentioned solvent, inclusive.

11. The method of deriving tetrakis (is fluorine, alkyl group and alkoxygroup, and if at least one of R1- R5and at least one of R6- R10is a fluorine atom, respectively, Xwithis a chlorine atom, bromine or iodine;

n = 2 or 3,

including the interaction of compounds (foradil)borane General formula 3

< / BR>
where each of R1- R5is a hydrogen atom, fluorine atom, alkyl group and alkoxygroup, and if at least one of R1- R5is a fluorine atom, Xbis an atom of fluorine, chlorine, bromine and iodine;

n = 2 or 3,

with a compound of General formula 4

< / BR>
where each of R6- R10is a hydrogen atom, fluorine atom, alkyl group and alkoxygroup, and if at least one of R6- R10is a fluorine atom, Xwithis a chlorine atom, bromine or iodine,

characterized in that interaction (foradil)borate and ferrimagnetic derived carried out in the solvent (d) containing diethyl ether and/or tetrahydrofuran and the third solvent having a higher boiling point than one of diethyl ether and/or tetrahydrofuran, after which diethyl ether and/or then it is carbonated the e crystals or solution.

12. The method according to p. 11, characterized in that the said compound (foradil)borate General formula 3 and the above-mentioned ferrimagnet derivative of General formula 4 are mixed with each other in the range between -20oC and the boiling point of the above-mentioned solvent, inclusive.

13. The method according to p. 11 where the above-mentioned compound (foradil)borane General formula 3 and the above-mentioned ferrimagnet derivative of General formula 4 interact with each other in the range between 30oC and the boiling point of the above-mentioned solvent, inclusive.

14. The method according to p. 11 where the above-mentioned compound (foradil)borane General formula 3 and the above-mentioned ferrimagnet derivative of General formula 4 interact with each other in the solvent (d) containing diethyl ether and/or tetrahydrofuran and connection with a higher boiling point than one of diethyl ether and/or tetrahydrofuran, after which diethyl ether and/or tetrahydrofuran is distilled off.

15. The method of deriving tetrakis(foradil)borate General formula 10

< / BR>
where each of R2- R4and R6- R10is a hydrogen atom, a fluorine atom, alkiline group or alkoxygroup, and if the edge is BR>
n is 2 or 3,

wherein the stage includes:

(A) interaction of halftoned General formula 6

< / BR>
where R2- R4described above

with halogen-substituted hydrocarbons of General formula 7

RaboutXand,

where Raboutis alkylenes, aryl, cycloalkyl or alkenylphenol group containing 2 to 12 carbon atoms, andanddescribed above

and magnesium in a solvent (a) containing diethyl ether and/or tetrahydrofuran, with the formation of ferrimagnetic derivative of General formula 8

< / BR>
where R2- R4Xanddescribed above;

(C) interaction ferrimagnetic derivative obtained in stage (a), with the boron halide of General formula

< / BR>
where Xinis an atom of fluorine, chlorine, bromine or iodine;

(C) adding the reaction solution to the solvent (b) having a higher boiling point than diethyl ether or tetrahydrofuran;

(D) distillation of diethyl ether and/or tetrahydrofuran to obtain (foradil)borane General formula 9

< / BR>
where R2- R4Xinand n described above,

(E) interaction mentioned (foradil)borane with ferrimagnetism derived total FEM, the solvent (C) has a boiling point of 60oC or higher.

17. The method according to p. 15, characterized in that the ratio of the halogen-substituted hydrocarbon with the General formula 7 to aristeidou General formula 6 is 0.5 or more equivalent.

18. The method according to p. 15, characterized in that the ratio of magnesium to aristeidou General formula 6 is 0.5 or more equivalent.

19. The method according to p. 15, characterized in that the halogen-substituted hydrocarbons of the General formula 7 and the solvent (a) are mixed with each other in the range between -20oC and the boiling point of the solvent (a) inclusive.

20. The method according to p. 15, characterized in that halftoned General formula 6 and halogen-substituted hydrocarbons of the General formula 7 interact with each other in the range between 30oC and the boiling point of the solvent (a) inclusive.

21. The method according to p. 15, characterized in that the molar ratio ferrimagnetic derivative of General formula 8 to the boron halide of General formula 2 is in the range of 1.0 to 5.0.

22. The method according to p. 15, characterized in that ferrimagnet derivative of General formula 8 and the boron halide of General formula 2 are mixed with each other at 80oC or below.

23. the uly 2 interact with each other in the range between 30oC and the boiling point of the solvent (a) inclusive.

24. The method of deriving tetrakis(foradil)borane General formula 11

< / BR>
where each of R2- R4is a hydrogen atom, fluorine atom, alkyl group or alkoxygroup;

Xandis a chlorine atom, bromine or iodine,

characterized in that halftoned General formula 6

< / BR>
where R2- R4described above

interacts with halogen-substituted hydrocarbon of the formula 7

RaboutXand,

where Raboutis alkyl, aryl, cycloalkyl, alkenylphenol groups containing 2 to 12 carbon atoms, and Xanddescribed above

and magnesium in one of the ether solvent (e), or a mixed solvent containing the aforementioned ether solvent (e) and a hydrocarbon solvent, with subsequent interaction formed ferrimagnetic derivative of formula 8

< / BR>
where R2- R4Xanddescribed above

with the boron halide of formula 2

< / BR>
where Xinis a fluorine atom, bromine, chlorine or iodine.

25. The method according to p. 24, characterized in that the ratio of the halogen-substituted hydrocarbon of formula 7 to aristeidou formula 6 silverado formula 6 is 0.5 or more for the equivalent.

27. The method according to p. 24, characterized in that ferrimagnet derivative of formula 8 and the boron halide of the formula 2 are mixed with each other in the range between -20oC and the boiling point of the solvent (e) or any used mixed solvent inclusive.

28. The method according to p. 24, characterized in that ferrimagnet derivative of formula 8 and the boron halide of formula 2 interact with each other in the range between 30oC and the boiling point of the solvent (e) or any used mixed solvent inclusive.

29. The method of deriving tetrakis(foradil)borate of the formula 13

< / BR>
where each of R2- R4and R11- R25are hydrogen atom, fluorine atom, alkyl group or alkoxygroup moreover, if at least one of R11- R25are fluorine atom, Xandis a chlorine atom, bromine or iodine,

characterized in that halftoned formula 6

< / BR>
where R2- R4described above

interacts with halogen-substituted hydrocarbon of the formula 7

RaboutXand< / BR>
where Xadescribed above;

Raboutis alkyl, aryl, cycloalkyl, alkenylphenol groups, barely, consisting of an ether solvent and hydrocarbon solvent, with subsequent interaction formed ferrimagnetic derivative of formula 8

< / BR>
where R2- R4Xadescribed above

with Tris(foradil)borane of the formula 12

< / BR>
where R11- R25above.

30. The method according to p. 29, characterized in that the ratio of the halogen-substituted hydrocarbon of formula 7 to aristeidou formula 6 is 0.5 or more for the equivalent.

31. The method according to p. 29, characterized in that the ratio of magnesium to aristeidou formula 6 is 0.5 or more for the equivalent.

32. The method according to p. 29, characterized in that ferrimagnet derivative of formula 8 and Tris(foradil)borane of formula 12 are mixed with each other in the range -20oC and the boiling point of the solvent (e) or any used mixed solvent.

33. The method according to p. 29, characterized in that ferrimagnet derivative of formula 8 and Tris(foradil)borane of the formula 12 interact with each other in the range between 30oC and the boiling point of the solvent (e) or any used mixed solvent inclusive.

 

Same patents:

The invention relates to a method of obtaining new fluorinated ariminium derivatives by reacting fluorinated aromatic compounds with halogenated hydrocarbon and magnesium in an ether solvent or in a mixture with hydrocarbon

The invention relates to the production of deisopentanisation

The invention relates to a new organoboron compound having catalytic activity, of the formula I

[RjM-Xd-MRj]a-bAc+(I)

in which R are, independently of one another, identical and denote C1-C40alkyl; X is, independently from each other, equal or different and denote C1-C40alkyl; M is, independently of one another, identical or different and denote an element of IIIa, IVa, Va group of the Periodic system of elements, provided that one M is boron, a is a cation of an element Ia, IIa and IIIa groups of the Periodic system of elements, carbene-hydronium - or sulfonyl - cation or compound Quaternary ammonium, and a is an integer from 0 to 10, b is an integer from 0 to 10, C is an integer from 0 to 10 and a = C; d is 1; j is an integer from 1 to 3
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The invention relates to methods of producing a cyclic boron compounds which may find application in the synthesis of 1,4-butandiol, cyclic ketones, tertiary alcohols, ethers and other products used in thin organic and ORGANOMETALLIC synthesis

The invention relates to methods of producing a cyclic boron compounds which may find application in the synthesis of TRANS-2,3-dialkyl-1,4-butandiol, substituted cyclic ketones, alcohols, esters, and other practically important compounds used in thin organic and ORGANOMETALLIC synthesis

FIELD: chemistry of organometallic compounds.

SUBSTANCE: invention relates to a method for preparing lithium complexes salts of the general formula (I): wherein each radical R3-R6 means hydrogen atom (H) or halogen atom (F, Cl or Br). Method involves mixing a) 3-, 4-, 5-, 6-substituted phenol of the formula (III): wherein R3-R6 have above given values with chlorosulfonic acid in acceptable solvent to yield compound of the formula (IV): ; b) intermediate product of the formula (IV) from the stage a) wherein R3-R6 have values given above is subjected for interaction with chlorotrimethylsilane to yield compound of the formula (II) given in the invention description and obtained product is filtered off and subjected for differential distillation; c) intermediate product (II) from the stage b) is subjected for interaction with tetramethanolate borate lithium (1-) in acceptable solvent and the end product (I) is isolated from it. Invention provides the development of a simple method for synthesis of lithium complex salts.

EFFECT: improved preparing method.

3 cl, 4 ex

FIELD: polymerization catalysts.

SUBSTANCE: invention relates to novel organometallic compounds and to olefin polymerization catalytic systems including such organometallic compounds, and also to a method for polymerization of olefins conduct in presence of said catalytic system. Novel organometallic compound is prepared by bringing into contact (i) compound of general formula I: (I), where Ra, Rb, Rc, and Rd, identical or different, represent hydrocarbon groups; and (ii) Lewis acid of general formula MtR

13
, where Mt represents boron atom and R1, identical or different, are selected from halogen and halogenated C6-C30-aryl groups.

EFFECT: enabled preparation of novel olefin polymerization cocatalysts, which reduce use of excess cocatalyst relative to alkylalumoxanes, do not lead to undesired by-products after activation of metallocene, and form stable catalytic compositions.

14 cl, 1 tbl, 32 ex

FIELD: chemistry of organophosphorus compounds.

SUBSTANCE: invention relates to compounds with the bond C-P, namely to phosphorus-boron-containing methacrylate that can be used as inhibitor of combustion of polyvinyl alcohol-base film materials. Invention describes phosphorus-boron-containing methacrylate of the following formula: wherein n = 4-8. Polyvinyl alcohol films modified with indicated phosphorus-boron-containing methacrylate shows the enhanced refractoriness, rupture strength up to 206 kgf/cm2, water absorption up to 240% and relative elongation up to 12%.

EFFECT: valuable properties of substance.

1 tbl, 2 ex

FIELD: chemistry of complex compounds.

SUBSTANCE: invention relates to new derivatives of boranocarbonate of the formula (I): wherein X1 means -H; X3 and X2 mean similar or different substitutes that are taken among the group consisting of -H, -NHxRy at x + y = 3, or -R wherein R means substitute that is bound with nitrogen or boron atom through carbon atom, respectively, and represents methyl or ethyl group; Y means group -OH, -OH2, -OR or -NHR wherein R means substitute that is bound with nitrogen or oxygen atom through carbon atom, respectively, and represents methyl or ethyl group; or their salts. Invention provides using prepared compounds as source of carbon monoxide (CO) and as a reducing agent in preparing carbonyl metal complexes in an aqueous solution. Also, invention involves a method for preparing borane carbonate and a method for reducing with using H3BCO as a reducing agent.

EFFECT: improved method for preparing.

20 cl, 14 ex

FIELD: organic synthesis.

SUBSTANCE: invention relates to organoboron compounds technology, in particular to aminoboranes and, more specifically, to trimethylaminoborane, which can be used as reducing and hydroboronizing agents as well as in color photography, in magnetic film manufacture, and as fuel additive to decrease amount of deposits in combustion chamber. Method comprises reaction of trimethylamine with gaseous diborane in organic solvent at reduced temperature. Solvent is selected from aliphatic, cycloaliphatic, and aromatic hydrocarbons with melting temperature not higher than -20°C. Reaction is conducted at temperature from -30°C to 0°C, preferably from -15 to -5°C, at trimethylamine-to-solvent volume ratio 1:(1/5-3.5).Proposed method simplifies preparation procedure owing to eliminated laborious solvent removing vacuum distillation stage and stage wherein of aqueous alkali metal hydroxide is introduced to stabilize aminoborane. Yield of desired product, characterized by high purity, achieves 95-98.6%, which is essentially higher than, for example yield (86%) of morpholinoborane regarded as prototype compound in a known process.

EFFECT: enhanced economical efficiency of process.

3 cl, 4 ex

FIELD: chemical technology.

SUBSTANCE: invention relates to technology for preparing organoboron compounds, in particular, to the improved method for preparing 9-borabicyclo[3.3.1]nonane. Method for preparing 9-borabicyclo[3.3.1]nonane is carried out by interaction of diborane with 1,5-cyclooctadiene in 1,4-dioxane medium at simultaneous feeding diborane and 1,5-cyclooctadiene at the rate necessary for maintaining the molar ratio 1,5-cyclooctadiene : diborane = (1.9-2.04):1.0, respectively, during all through reaction. The process is carried out in the volume ratio 1,4-dioxane : 1,5-cyclooctadiene = (2.2-4.0):1.0 and at temperature 11-25°C. In preparing 9-borabicyclo[3.3.1]nonane the reaction mass is kept at temperature 65-102°C. The invention provides simplifying technology in preparing 9-borabicyclo[3.3.1]nonane due to exclusion the preliminary preparing borane complex and additional recrystallization of 9-borabicyclo[3.3.1]nonane, enhancing yield of the end product up to 91.0-93.5% of the high quality (the content of basic substance is 99.1-99.9%, melting point is 152-156°C), and possibility for creating the wasteless manufacturing. Method for preparing 9-borabicyclo[3.3.1]nonane shows technological simplicity in its realization and economy profit in its realization in industrial scale.

EFFECT: improved preparing method.

4 cl, 4 ex

FIELD: chemical technology.

SUBSTANCE: invention relates to technology for preparing organoboron compounds, in particular, pinacol borane (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) representing a monofunctional hydride-borating agent for alkenes and alkynes and for Suzuki's cross-coupling reaction also. Method is carried out by interaction of pinacol (2,2,3,3-tetramethylethylene glycol, 2,3-dimethyl, 2,3-butanediol) with borane reagent in the presence of a solvent and the following isolation of the end product. Gaseous diborane is used as a borane reagent and the process is carried out in diethyl ether medium at range of temperatures 5-36°C, and the process is carried out in the mole ratio of reagents pinacol : diborane = 1:(0.45-0.55), respectively; or the method is carried out by interaction of pinacol with borane reagent and the following isolation of the end product wherein gaseous diborane is used as a borane reagent, and the process is carried out in pinacol melt at temperature ranges 40-80°C. The process is carried in the mole ratio of reagents pinacol : diborane = 1:(0.45-0.55), respectively. Method provides preparing pinacol borane with high yield 90-95% and high purity 99.5-99.8%. Method shows technological simplicity and economy profit in realization in the industrial scale.

EFFECT: improved preparing method.

3 cl, 4 ex

FIELD: organic chemistry, pharmaceuticals.

SUBSTANCE: disclosed method for production of [R-(R*,R*)}]-2-(4-fluoriphenyl)-β,δ-dihydroxy-5-(1-methyl)-3-phenyl-4-[(phenylamino)-carbonyl]-1H-heptanoic acid semi-calcium salt (atorvastatin) of formula XII includes reaction of preprepared compound of formula Xa with compound of formula IV in solvent mixture selected from group containing xylene, cyclohexane, methyl-tert-butyl ether, diisopropyl ether, acetonitrile, in presence of catalyst selected from group containing pivalic acid, trifluotomethylsulfonic acid, methanesulfonic acid or p-toluenesulfonic acid to form intermediate of formula XIa , followed by hydrolysis of formula XIa and calcium salt production to form target product of formula XII. Claimed compound represents enzyme hydroxymethylglutaryl-CoA reductase inhibitor, and thereby is useful as hypolipidemic and hypocholesteronemic agents.

EFFECT: new method for atorvastatin synthesis.

7 cl, 2 dwg, 9 ex

FIELD: polymer materials.

SUBSTANCE: invention provides luminescent material showing semiconductor properties and being product of complex polymerization in glow discharge, which is formed as a supported polymer layer located either between electrodes or on any of electrodes. Starting pyrromethene complex is difluoroborate complex of 1,3,5,7,8-pentamethyl-2,6-diethylpyrromethene (Pyrromethene 567). Method of preparing luminescent semiconductor polymer material comprises glow-discharge polymerization for 2 to 120 min of Pyrromethene 567 vapors at temperature preferably 250-350°C, pressure 10-1 to 10-2 Pa, and discharge power 0.5-3 W. Resulting luminescent polymer is characterized by thickness preferably 0.001-10 μm, conductivity 1·10-10 to 5·10-10 Ohm-1cm-1 (20°C), luminescence emission maximum in the region of 540-585 nm at band halfwidth 55-75 nm. Polymer is obtained with quantum yield 0.6-0.8 and is designed for creation of film light-emitting devices.

EFFECT: improved performance characteristics of material.

13 cl, 3 ex

FIELD: physical analytical methods.

SUBSTANCE: invention relates to bioanalytical methods involving dye-labeled indicators. Bioanalytical method without separation is provided directed to measure analyte obtained from biological liquid or suspension, wherein are used: analyte microparticles as first biospecific reagent; and second biospecific reagent labeled with biphotonic fluorescent dye based on dipyrromethene boron difluoride containing at least one water solubility imparting group selected from ammonium salt and sulfonic or carboxylic acid alkali metal salt and at least one chemically active group selected from carboxylic acid, reactive carboxylic acid ester, carboxylic acid anhydride, maleimide, amine and isothiocyanate. In the method of invention, laser is focused onto reaction suspension and biphotonically excited fluorescence from individual microparticles (randomly flowing or oriented by pressure provided by emission of exciting laser through focal volume of laser beam).

EFFECT: increased efficiency of bioanalyses.

5 cl, 5 dwg, 5 tbl, 25 ex

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