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Preparing method for 3,4,5-trifluorophenylboronic acid

A technology of trifluorophenylboronic acid and trifluorobromobenzene, which is applied in the field of preparation of 3,4,5-trifluorophenylboronic acid, can solve the problems such as the purity of the final product cannot meet the specification, fluorine loss, and inapplicability, and reduce the The effect of input cost, simplified process and high purity

Inactive Publication Date: 2015-11-25
BENGBU CHINA SYNCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has multiple disadvantages. First, the boiling point of anhydrous diethyl ether is 35° C., which is too low to be suitable for large-scale production. Second, the use of magnesium metal to prepare Grignard reagents will lead to the generation of some fluorine-removing products, which will cause The purity of the final product does not meet the specifications of electronic-grade raw materials required for liquid crystal materials; third, the reaction with trimethyl borate is carried out at -78°C, which requires special low-temperature equipment, making this method unsuitable for the production of general equipment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Glass three-necked reaction flask equipped with mechanical stirring, thermometer, constant pressure dropping funnel, add solvent tetrahydrofuran and raw material 3,4,5-trifluorobromobenzene, carry out nitrogen replacement, add dropwise 1.1 molar equivalent of isopropyl at 10-15°C The magnesium chloride solution was reacted for 1 hour after the dropwise addition was completed, and the reaction of the raw material 3,4,5-trifluorobromobenzene was detected through the central control of gas chromatography. Then, 1.2 molar equivalents of trimethyl borate was added dropwise at 5-10° C., reacted for 2 hours, and post-treated. After treatment, add a certain amount of water to terminate the reaction, adjust the pH value of the system to acidity with acid, separate the organic phase, remove the solvent by distillation under reduced pressure, and obtain the product 3,4,5-trifluorophenylboronic acid after recrystallization, with a purity greater than 99.5 %, relevant impurities are...

Embodiment 2

[0015] Glass three-necked reaction flask equipped with mechanical stirring, thermometer, constant pressure dropping funnel, add solvent tetrahydrofuran and raw material 3,4,5-trifluorobromobenzene, carry out nitrogen replacement, drop 1.2 molar equivalent of isopropyl at 0-10°C The magnesium chloride solution was reacted for 2 hours after the dropwise addition was completed, and the reaction of the raw material 3,4,5-trifluorobromobenzene was detected through the central control of gas chromatography. Then, 1.3 molar equivalents of trimethyl borate was added dropwise at 15-20° C., reacted for 1 hour, and post-treated. After treatment, add a certain amount of water to terminate the reaction, adjust the pH value of the system to acidity with acid, separate the organic phase, remove the solvent by distillation under reduced pressure, and obtain the product 3,4,5-trifluorophenylboronic acid after recrystallization, with a purity greater than 99.5 %, relevant impurities are less th...

Embodiment 3

[0017] Glass three-necked reaction flask equipped with mechanical stirring, thermometer, constant pressure dropping funnel, add solvent tetrahydrofuran and raw material 3,4,5-trifluorobromobenzene, carry out nitrogen replacement, add 1.3 molar equivalent of isopropyl The magnesium chloride solution was reacted for 3 hours after the dropwise addition was completed, and the reaction of the raw material 3,4,5-trifluorobromobenzene was detected through the central control of gas chromatography. Then, 1.4 molar equivalents of trimethyl borate was added dropwise at 20-25° C., reacted for 1 hour, and post-treated. After treatment, add a certain amount of water to terminate the reaction, adjust the pH value of the system to acidity with acid, separate the organic phase, remove the solvent by distillation under reduced pressure, and obtain the product 3,4,5-trifluorophenylboronic acid after recrystallization, with a purity greater than 99.5 %, relevant impurities are less than 200PPM. ...

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Abstract

The invention discloses a preparing method for 3,4,5-trifluorophenylboronic acid and relates to the technical field of organic synthesis. Tetrahydrofuran as reaction solvent and 1-bromo-3,4,5-trifluorobenzene as a reaction raw material react with isopropyl magnesium chloride in a Grignard exchanging mode to prepare 3,4,5-trifluoro phenylmagnesium chloride, and then 3,4,5-trifluoro phenylmagnesium chloride reacts with trimethyl borate in a boric acidifying mode to prepare the 3,4,5-trifluorophenylboronic acid. The target product 3,4,5-trifluorophenylboronic acid is prepared by means of a one-pot method, the technology is simplified, the investment cost is reduced, no special production equipment is needed in the preparation process, and the 3,4,5-trifluorophenylboronic acid is suitable for industrialized safety production; the product 3,4,5-trifluorophenylboronic acid is high in purity, and the purity grade of an electronic-grade fluorine-contained liquid crystal raw material can be achieved.

Description

Technical field: [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 3,4,5-trifluorophenylboronic acid. Background technique: [0002] 3,4,5-trifluorophenylboronic acid can be used as an intermediate of fluorine-containing liquid crystal materials to prepare new fluorine-containing liquid crystal materials. In addition, 3,4,5-trifluorophenylboronic acid is also an intermediate for preparing the pesticide flufenapyramide. Therefore, the research on the preparation method of 3,4,5-trifluorophenylboronic acid has important economic value. [0003] Patent CN102093245A mentions a method for preparing 2,4,5-trifluorophenylboronic acid from 2,4,5-trifluorobromobenzene. The method uses metal magnesium, in the solvent anhydrous ether, through the Grignard reaction, from 2,4,5-trifluorobromobenzene to prepare 2,4,5-trifluorophenylmagnesium bromide, and then at -78 ° C It reacts with trimethyl borate and prepares 2,4,5-tr...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 杨青张浩赵士民徐剑霄汪洪湖
Owner BENGBU CHINA SYNCHEM TECH CO LTD
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