Method for preparing 2-hydroxybenzeneboronic acid

A technology of hydroxybenzene boronic acid and hydroxyl group, applied in the field of preparing 2-hydroxybenzene boronic acid, can solve the problems of high price of 2-bromophenol, unsuitable for large-scale industrial production of 2-hydroxy benzene boronic acid, increase in production cost, etc. Purification steps, convenient large-scale production, and the effect of saving production costs

Active Publication Date: 2014-05-21
BENGBU CHINA SYNCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method prepares 1 mole of 2-hydroxyphenylboronic acid, and at least 2 moles of n-butyllithium need to be consumed, which greatly increases the production cost, and the price of raw material 2-bromophenol is relatively high, so it is not suitable for large-scale industrial production of 2-hydroxyphenylboronic acid. boric acid

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A 10-liter glass reactor is equipped with a mechanical stirrer, a thermometer, and a constant-pressure dropping funnel. Under nitrogen protection, 940 g of raw material phenol and 940 g of dihydropyran are added, and 94 g of catalyst pyridine p-toluenesulfonate is added under stirring for 8 hours of reaction. Distill under reduced pressure at 60°C to remove low boilers in the system; then add 3000g tetrahydrofuran to the reaction flask, lower the temperature to -80°C with respect to 1.2 equivalents of triisopropyl borate relative to phenol, and dropwise add 1.5 equivalents of triisopropyl borate relative to phenol n-Butyllithium, continue to react at -80°C for 8 hours after dropping, slowly raise the temperature of the reaction solution to -30°C, add 2000g of water to the system, adjust the pH value to 1 with hydrochloric acid, react at 30°C for 2 hours, Distill under reduced pressure at ℃, remove the solvent in the system, add 3000g of water, reflux for 2 hours, cool do...

Embodiment 2

[0025] A 10-liter glass reactor is equipped with a mechanical stirrer, a thermometer, and a constant-pressure dropping funnel. Under nitrogen protection, 940 g of raw material phenol and 940 g of dihydropyran are added, and 94 g of catalyst pyridine p-toluenesulfonate is added under stirring, and the reaction is carried out for 8 hours. ℃ under reduced pressure distillation to remove the low boilers in the system; then add 3000g tetrahydrofuran to the reaction flask, lower the temperature to -80℃ with respect to 1.2 equivalents of trimethyl borate relative to phenol, and dropwise add 1.5 equivalents of n-butyl borate relative to phenol Lithium, continue to react at -80°C for 8 hours after dropping, slowly raise the temperature of the reaction solution to -30°C, add 2000g of water to the system, adjust the pH value to 1 with hydrochloric acid, react at 30°C for 2 hours, and reduce pressure at 60°C Distill to remove the solvent in the system, add 3000g of water, reflux for 2 hour...

Embodiment 3

[0027] A 10-liter glass reactor is equipped with a mechanical stirrer, a thermometer, and a constant-pressure dropping funnel. Under nitrogen protection, 940 g of raw material phenol and 940 g of dihydropyran are added, and 94 g of catalyst pyridine p-toluenesulfonate is added under stirring, and the reaction is carried out for 8 hours. ℃ Distillation under reduced pressure to remove low boilers in the system. Then add 3000g tetrahydrofuran to the reaction flask, lower the temperature to -80°C with respect to 1.2 equivalents of trimethyl borate relative to phenol, dropwise add 1.2 equivalents of n-butyllithium relative to phenol, and continue to react at -80°C for 8 hours after dropping. Slowly raise the temperature of the reaction solution to -30°C, add 2000g of water to the system, adjust the pH value to 1 with hydrochloric acid, react at 30°C for 2 hours, distill under reduced pressure at 60°C, remove the solvent in the system, add 3000g of water, and reflux for 2 hours. ho...

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Abstract

The invention provides a method for preparing 2-hydroxybenzeneboronic acid, which relates to the technical field of industrial production for 2-hydroxybenzeneboronic acid. The method is characterized by comprising the following steps of: selecting raw material phenol which is already commercialized in the market as an initial raw material, in a normal-temperature condition, protecting hydroxyl at first, and then directly dripping n-butyllithium in the mixture of protected hydroxyl intermediate and borate compounds without separating crude products, and after the reaction is finished, hydrolyzing to prepare 2-hydroxybenzeneboronic acid. The method is easily-available in raw materials, high in both the purity and yield of the reaction product, stable in process conditions, simple to operate and suitable for large-scale production, and provides novel thinking and method for preparing 2-hydroxybenzeneboronic acid.

Description

technical field [0001] The invention relates to the technical field of industrial production of 2-hydroxyphenylboronic acid, in particular to a method for preparing 2-hydroxyphenylboronic acid. Background technique [0002] 2-Hydroxyphenylboronic acid is an important molecular fragment for the preparation of new drugs for the treatment of diabetes. It is also an important organic synthetic medicine and pesticide intermediate. It is widely used in Suzuki cross-coupling reactions and is a key intermediate for the preparation of 2-hydroxybiphenyl compounds. . Therefore, it is of great significance to develop a high-efficiency, low-cost 2-hydroxyphenylboronic acid synthesis process. [0003] Present stage, the method for preparing 2-hydroxyphenylboronic acid mainly contains following several kinds: [0004] 1. Use 2-hydroxyphenylboronic acid pinacol ester as raw material [Tetrahedron Letters, Vol.45, 2004, p6657-6660], hydrolyze with hydrochloric acid in acetonitrile solvent t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
Inventor 杨青张浩赵士民徐剑霄刘兴华
Owner BENGBU CHINA SYNCHEM TECH CO LTD
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