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Process for synthesizing 2-cyanogroup 3-fluorophenylboronic acid

A technology of fluorophenylboronic acid and cyano group is applied in the field of synthesis of 2-cyano 3-fluorobenzeneboronic acid, which can solve the problems of no relevant literature reports, and achieve the effects of improving product yield, good process stability and high purity

Inactive Publication Date: 2017-07-25
DALIAN NETCHEM CHIRAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The boronic acid compound 2‐nitrile‐3‐fluorophenylboronic acid synthesized by this application has no relevant literature reports at present

Method used

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  • Process for synthesizing 2-cyanogroup 3-fluorophenylboronic acid

Examples

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Effect test

Embodiment 1

[0027] a) Synthesis of 2‐fluoro6‐bromobenzaldehyde: Add 0.66mol of diisopropylamine and 50g of anhydrous ether to a nitrogen-protected four-necked flask, drop the temperature to -40°C to -50°C, add 1.25mol of n-butyllithium dropwise, and stir Keep warm for 1 hour, and the reaction of raw materials is completed. Cool down to -70°C to -80°C, add dropwise a mixed solution of 0.29mol m-fluorobromobenzene and 120g anhydrous ether, and stir for 2 hours after the dropwise addition. Afterwards, 0.38 mol of dimethylformamide was added dropwise, stirred for 1 hour, and quenched with acetic acid at pH=1-2. The oil layer was extracted with methyl tert-butyl ether and distilled under vacuum under reduced pressure to obtain the intermediate 2-fluoro-6-bromobenzaldehyde with a GC purity of 99%.

[0028] b) Synthesis of 2-fluoro-6-bromoxynil: Add 0.2mol of 2-fluoro-6-bromobenzaldehyde, 0.4mol of hydroxylamine hydrochloride, and 150g of formic acid into a 1L single-necked bottle, heat up at 1...

Embodiment 2

[0031] a) Synthesis of 2‐fluoro6‐bromobenzaldehyde: Add 268 g of diisopropylamine and 100 g of tetrahydrofuran into a nitrogen-protected four-neck flask, cool down to -40°C to -50°C, and dropwise add 340 g of Butyllithium was stirred and kept warm for 1 hour, and the reaction of the raw materials was completed. Cool down to -70°C to -80°C, add dropwise a mixed solution of 200g m-fluorobromobenzene and 100g tetrahydrofuran, and stir for 2 hours after the dropwise addition. Afterwards, 112 g of dimethylformamide was added dropwise, stirred for 1 hour, and quenched with hydrochloric acid to pH=1-2. Ethyl acetate extracted the oil layer and distilled it under vacuum under reduced pressure to obtain 165 g of 2-fluoro-6-bromobenzaldehyde with a GC purity of 98%.

[0032] b) Synthesis of 2-fluoro-6-bromoxynil: add 165g of 2-fluoro-6-bromobenzaldehyde, 114g of hydroxylamine hydrochloride, and 450g of formic acid into a 2L single-necked bottle, heat up at 100°C and reflux for 2 hours,...

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Abstract

The invention relates to a process for synthesizing 2-cyanogroup 3-fluorophenylboronic acid. According to the method, 3-bromofluorobenzene is used as a raw material, and takes a reaction with LDA and dimethylformamide in a tetrahydrofuran solvent to obtain 2-fluorine 6-bromobenzaldehyde; then, the 2-fluorine 6-bromobenzaldehyde and hydroxylamine hydrochloride take a reaction at 100 DEG C to obtain 2-fluorine 6-bromoxynil; finally, triisopropyl borate is added into the intermediate; n-butyllithium is dropwise added at -70 DEG C; reduced pressure distillation is performed to obtain 2-fluorine 6-bromophenylboronic acid. The process provided by the invention has the advantages that the operation is simple and convenient; the raw material can be easily obtained; the yield is high.

Description

technical field [0001] The invention relates to a process for synthesizing 2-cyano-3-fluorophenylboronic acid, which belongs to the field of chemical technology. [0002] Background technique: [0003] Due to the good adaptability and functional group tolerance of the reaction substrate, the Suzuki coupling reaction is not only often used in the preparation of compounds such as olefins and biphenyls in organic synthesis, but also widely used in the fields of pharmaceuticals, electronics, and materials. [0004] The boronic acid compound 2-cyano-3-fluorophenylboronic acid synthesized by this application has no relevant literature reports at present. Contents of the invention [0005] The purpose of the present invention is to overcome above-mentioned insufficient problem, provide a kind of technique of synthesizing 2-cyano-3-fluorophenylboronic acid, process stability is good, easy and simple to operate, productive rate is high, be easy to industrialized production. [0006...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 刘启宾王忠兴
Owner DALIAN NETCHEM CHIRAL TECH
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