Method for preparing pinacol borane (variants)

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

 

The invention relates to the technology for pinacolborane (4,4,5,5-tetramethyl-1,3,2-dioxaborolane), which can be used as monofunctional hydroperiodide agent for alkenes and alkynes, as well as in reactions with formation of carbon-carbon, such as reaction cross-combination Suzuki.

A method of obtaining organoboron compounds of catecholborane (1,3,2-benzodioxole) reaction of diatomic phenol - pyrocatechin with DIBORANE in diethyl ether (patent RU 2206569 S1). In accordance with the description of this patent catecholborane get interaction pyrocatechin with boranova reagent, which is used gaseous DIBORANE in the presence of solvent diethyl ether at a molar ratio of reagents pyrocatechin:DIBORANE, equal to 1:(0.4 to 0.5), respectively, at a temperature in the range from -10 to +10°C. This method provides receiving of catecholborane with access 88,0-92,0% and a purity of 99.7-100.0%a.

The closest analogue to the claimed invention in its technical essence is the method of receiving pinacolborane by the interaction of pinacol (2,2,3,3-tetraethyleneglycol, 2,3-dimethyl-2,3-butanediol) with borane-dimethylsulfide complex at low temperature (Charles E. Tucker, Jessica Davidson, Paul Knochel, J. Org. Chem., 57, 3482-3485, 1992). Because pyrocatechin and pin the number belong to different groups, oxygen-containing compounds, what affects their reactivity towards boranova reagents. Pyrocatechin is a typical representative of a group of organic compounds - diatomic phenols, and how all of the phenol is a weak acid (pKa=5,18) due to delocalization of pairs of electrons of the oxygen atoms in the side of the benzene ring. In the molecule of pinacol, which is representative of a group of organic compounds - aliphatic diols, no delocalization pair electrons of oxygen, which affects its reactivity towards electrophilic boranova reagents. The different distribution of the electron density at the oxygen atoms to influence the mechanism of the reaction, and the direction of chemical reactions, i.e. the selectivity of the formation of the target product. So in contrast to the method of obtaining pinacolborane the prototype attempts of the applicant to obtain catecholborane interaction pyrocatechin and borane-dimethylsulfide complex led to a negative result, because in the interaction of pyrocatechin and borane-dimethylsulfide complex was formed only Tris(catecholate)bisbort and was practically formed catecholborane

Pinacolborane prototype is produced by adding 10 M borane-dimethylsulfide complex to a solution of pinacol to dry the dichloromethane at 0° With and effective mixing (equation 1).

The molar ratio of the reagents pinacol:borane-dimethylsulfide complex is 1:1. When you are finished adding the borane-dimethylsulfide complex to a solution of pinacol the reaction mass is stirred at 0°C for 1 hour and then at 25°C for 1 hour. Pinacolborane can be selected according to this method, vacuum distillation (42÷43°/50 mm Hg) to yield 63%. Selected pinacolborane contains less than 1% of dimethyl sulphide.

The above method has several disadvantages, namely:

low yield of the product;

- prior receipt of borane-dimethylsulfide complex leads to the complexity of the process as a whole;

- used as boranova reagent is borane-dimethylsulfide complex has a very persistent odor even in low concentrations;

- released from the reaction of dimethyl sulfide and the solvent is dichloromethane have similar boiling point (36°s and 40°respectively), which significantly complicates the process of their separation.

The objective of the invention is to develop a technically simple method of obtaining pinacolborane high yield of the final product and a high content of the basic substance.

DL is solving the problem proposed group of inventions, United by a single inventive concept.

Option 1. The problem is solved by a method of obtaining pinacolborane, including the interaction of pinacol with boranova reagent in the solvent environment and the subsequent allocation of the target product, according to the invention as boranova reagent using gaseous DIBORANE and the process is executed in the environment of diethyl ether, and the reaction is carried out at a temperature in the range from 5 to 36°when the molar ratio pinacol:DIBORANE, equal to 1:(0,45-0,55), respectively.

Experimental studies have shown that the best solvent for the implementation of the proposed method is diethyl ether. Conducting the reaction in the environment diethyl ether allows you to get pinacolborane with high yield and high content of the basic substance.

The upper temperature limit for the receipt of pinacolborane in diethyl ether is determined by the boiling point of the employed solvent (tKip.=36°). The lower temperature limit is 5°S, is determined by the fact that when carrying out the process at lower temperatures the yield remains constant, and the processing at the high cost of cooling is impractical.

The selected molar ratio of reagents pinacol:DIBORANE, equal to 1:(0,45-0,5), respectively, is optimal, because the reduction in the number of gaseous DIBORANE reduces the yield of the target product from leaking adverse reactions between pinacolborane and penacola, and its increase is not economically feasible.

The combination of all the essential features set forth in the proposed method of obtaining pinacolborane for option 1 allows you to get pinacolborane with high yield and high content of the basic substance.

Below is a description of the proposed method of obtaining pinacolborane for option 1.

The process is carried out in a batch reactor, the equipped with a bubbler for supplying gaseous DIBORANE, a stirrer, a reflux condenser, a water seal to prevent air from entering the system. The pre-reactor otdovat inert gas such as nitrogen. Loaded into the reactor solution pinacol in diethyl ether, and establish a temperature selected from a range from 5 to 36°C. If the set temperature is reached, start the dosage of DIBORANE with vigorous stirring of the reaction mass. The molar ratio of the reagents pinacol:DIBORANE is 1:(0,45-0,55). After the completion of dosing of DIBORANE reaction mass for a more complete bonding of DIBORANE and pinacol maintained at a temperature in the range from 5 to 36°each is 15-60 minutes with stirring. Then the reaction mass otdovat nitrogen to avoid the formation of by-products at the stage of selection of the target product. Pinacolborane separated from the reaction mass by vacuum distillation.

The output of pinacolborane by this method is 90-95%, the content of the basic substance of 99.5-99.8 per cent.

Below are examples which explain the invention by variant 1.

Example 1. In the reactor, purged with nitrogen, charged with 35 g of pinacol (296 mmol) and 121 g (170 ml) diethyl ether. Cool the contents of the reactor to 10°C. To the solution pinacol with vigorous stirring for 2 hours serves gaseous DIBORANE in the amount of 3.75 g (136 mmol), maintaining the temperature in the reactor 10°C. the Molar ratio of pinacol:DIBORANE is 1:0,46.

After the filing of DIBORANE maintain the reaction mass at a temperature of 10°under stirring for 1 hour. Unreacted DIBORANE otdovat from the reaction mixture with nitrogen.

Pinacolborane separated from the reaction mass by vacuum distillation.

The output of pinacolborane is 33,13 g (95%), the content of the basic substance is 99.8%.

Example 2. The method is carried out analogously to example 1. The process is carried out at a temperature of 30°when the molar ratio pinacol:DIBORANE, equal to 1:0.5 in.

The output of pinacolborane is 91%, the content of the primary in the society 99,6%.

Option 2. The problem is solved by a method of obtaining pinacolborane, including the interaction of pinacol with boranova reagent and the subsequent allocation of the target product, according to the invention as boranova reagent using gaseous DIBORANE and the process is carried out in the melt penacola, the reaction is carried out at a temperature in the range from 40 to 80°when the molar ratio pinacol:DIBORANE, equal to 1:(0,45-0,55), respectively.

The lower temperature limit for the receipt of pinacolborane 40°is determined by the melting temperature of pinacol (40-43°). Thus, the process of obtaining pinacolborane occurs when the interaction of gaseous DIBORANE with the liquid phase (molten) pinicola. When carrying out the process at temperatures above 80°With reduced output of pinacolborane due to the occurrence of adverse reactions interaction of pinacolborane and pinacol, and thermal instability of pinacolborane at these temperatures.

The selected molar ratio of reagents pinacol:DIBORANE, equal to 1:(0,45-0,55), respectively, is optimal, because the reduction in the number of gaseous DIBORANE reduces the yield of the target product from leaking adverse reactions between pinacolborane and penacola, and increase the cost necelesobrazno is about, in addition, the excess DIBORANE leads to the formation of side products of the highest borovodorodam that reduce the purity of pinacolborane.

The combination of all the essential features set forth in the proposed method of obtaining pinacolborane for option 1 allows you to get pinacolborane with high yield and high content of the basic substance.

Below is a description of the proposed method of obtaining pinacolborane for option 2.

The process is carried out in a batch reactor, the equipped with a bubbler for supplying gaseous DIBORANE, a stirrer, a reflux condenser, a water seal to prevent air from entering the system. The pre-reactor otdovat inert gas such as nitrogen. In the reactor load pinacol. Pinacol in the reactor is heated to a temperature in the range from 40 to 80°C. If the set temperature is reached, start the dosage of DIBORANE with vigorous stirring of the reaction mass. The molar ratio of the reagents pinacol:DIBORANE is 1:(0,45-0,55), respectively. After the completion of dosing of DIBORANE reaction mass for a more complete bonding of DIBORANE and pinacol maintained at a temperature in the range from 40 to 80°C for 15-60 minutes with stirring. Then the reaction mass otdovat nitrogen to avoid the formation of side products is s at the stage of selection of the target product. Pinacolborane separated from the reaction mass by vacuum distillation.

The output of pinacolborane by this method is 90-95%, the content of the basic substance of 99.5-99.8 per cent.

Below are examples which explain the invention by variant 2.

Example 1. In the reactor, purged with nitrogen, charged 50 g of pinacol (423 mmol) and heated the contents of the reactor to 50°C. To melt pinacol with vigorous stirring for 2 hours serves gaseous DIBORANE in the number of 5.24 g (190 mmol), maintaining the temperature in the reactor 50°C. the Molar ratio of pinacol:DIBORANE is 1:0,45.

After the filing of DIBORANE maintain the reaction mass at a temperature of 50°under stirring for 15 minutes. Unreacted DIBORANE otdovat from the reaction mixture with nitrogen.

Pinacolborane separated from the reaction mass by vacuum distillation.

Output: 46,25 g pinacolborane (95%), the content of the basic substance of 99.9%.

Example 2. The method is carried out analogously to example 1. The process is carried out at a temperature of 70°when the molar ratio pinacol:DIBORANE, equal to 1:0.5 in.

The output of pinacolborane is 90%, the content of the basic substance of 99.5%.

Thus, we developed a new method of obtaining pinacolborane allows you to get pinacolborane with a high yield of 90-95% (on prototype 63%) and high soda is the content of the basic substance of 99.5-99.8 per cent and technologically simple to implement.

1. The method of receiving pinacolborane, including the interaction of pinacol with boranova reagent in the solvent environment and the subsequent allocation of the target product, characterized in that as boranova reagent using gaseous DIBORANE, the process is executed in the environment of diethyl ether at a temperature in the range from 5 to 36°and a molar ratio pinacol:DIBORANE, equal 1:(0,45-0,55).

2. The method of receiving pinacolborane, including the interaction of pinacol with boranova reagent, characterized in that as boranova reagent using gaseous DIBORANE, the process is carried out in the melt pinacol at a temperature in the range from 40 to 80°and a molar ratio pinacol:DIBORANE, equal 1:(0,45-0,55).



 

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