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Preparation method of 4-hydroxymethyl phenylboronic acid

A technology of hydroxymethylphenylboronic acid and hydroxyl protection agent, which is applied in the field of preparation of 4-hydroxymethylphenylboronic acid, can solve the problems of high preparation cost, low yield and low purity of 4-hydroxymethylphenylboronic acid, and achieves the The effect of low production cost, environmental friendliness and simple operation

Active Publication Date: 2021-09-07
宁夏中星显示材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Aiming at the problems of low yield, low purity and high production cost in the existing process for preparing 4-hydroxymethylphenylboronic acid, the invention provides a method for preparing 4-hydroxymethylphenylboronic acid

Method used

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  • Preparation method of 4-hydroxymethyl phenylboronic acid
  • Preparation method of 4-hydroxymethyl phenylboronic acid
  • Preparation method of 4-hydroxymethyl phenylboronic acid

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Experimental program
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Embodiment 1

[0056] The embodiment of the present invention provides a preparation method of 4-hydroxymethylphenylboronic acid, comprising the following steps:

[0057] Step 1. Under the protection of nitrogen, put 93.5g of p-bromobenzyl alcohol and 37.4g of imidazole in a 1000mL three-necked flask, add 270mL of dichloromethane, stir well, and add tert-butyldimethyl chloride dropwise in an ice-water bath at 5°C Silane solution (79.1g of tert-butyldimethylsilyl chloride dissolved in 180mL of dichloromethane), temperature controlled at 0°C to 10°C and added dropwise for 50 minutes, after the dropwise addition was completed, heated to 30°C, reacted for 2 hours, then After treatment, 144.6 g of crude tert-butyldimethylsiloxymethylene bromide represented by formula VIII was obtained, with a yield of 95.1% and a purity of 99.1%;

[0058]

[0059] Step 2, under the protection of nitrogen, dissolve the crude product of tert-butyldimethylsiloxymethylene bromide benzene in 300mL tetrahydrofuran t...

Embodiment 2

[0063] Embodiments of the present invention provide a method for preparing 4-hydroxymethylphenylboronic acid, comprising the following steps:

[0064] Step 1. Under the protection of nitrogen, put 93.5g of p-bromobenzyl alcohol and 75.9g of triethylamine into a 1000mL three-necked flask, add 190mL of tetrahydrofuran, stir well, and add phenyldimethylchlorosilane dropwise in an ice-water bath at 5°C solution (93.9g of phenyldimethylsilyl chloride dissolved in 460mL of tetrahydrofuran), temperature-controlled at 10°C to 15°C and added dropwise for 60 minutes, after the dropwise addition was completed, heated to 40°C, reacted for 4 hours, and post-processed to obtain formula X The crude product phenyldimethylsiloxymethylene bromide benzene 154.3g, yield 95.3%, purity 99.2%;

[0065]

[0066] Step 2, under the protection of nitrogen, dissolve the crude product of phenyldimethylsiloxymethylene bromide benzene in 770mL ether to obtain the ether solution of phenyldimethylsiloxymet...

Embodiment 3

[0070] Embodiments of the present invention provide a method for preparing 4-hydroxymethylphenylboronic acid, comprising the following steps:

[0071] Step 1. Under nitrogen protection, put 93.5g of p-bromobenzyl alcohol and 95.4g of sodium carbonate in a 1000mL three-necked flask, add 370mL of ether, stir well, and add dropwise triethylchlorosilane solution (98.0 g triethylchlorosilane dissolved in 340mL tetrahydrofuran), temperature controlled at 15°C to 25°C and added dropwise for 50min, after the dropwise addition was completed, heated to 30°C, reacted for 2h, post-processed to obtain the crude product III shown in formula XII Ethylsiloxymethylene bromide benzene 144.7g, yield 95.3%, purity 99.2%;

[0072]

[0073] Step 2, under the protection of nitrogen, the above crude triethylsiloxymethylene bromide benzene was dissolved in 430mL dioxane to obtain a dioxane solution of triethylsiloxymethylene bromide benzene, which was then Add dropwise to a 1000mL three-necked fla...

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Abstract

The invention relates to the technical field of organic synthesis, and particularly discloses a preparation method of 4-hydroxymethyl phenylboronic acid. The preparation method comprises the following steps: taking p-bromobenzyl alcohol as a raw material, preparing a Grignard reagent through hydroxyl protection and Grignard reaction, then performing addition reaction on the prepared Grignard reagent and a boronizing reagent, and finally performing hydrolysis deprotection through acidic ionic liquid, thereby obtaining the target product 4-hydroxymethyl phenylboronic acid. According to the preparation method, stable existence of the 4-hydroxymethyl phenylboronic acid under the hydrolysis condition can be ensured, side reactions are reduced, the total yield of the product can reach 80% or above, the HPLC content is greater than 99.5%, the raw materials are easy to obtain, the operation is simple, the safety is high, and industrial production of the 4-hydroxymethyl phenylboronic acid is realized.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 4-hydroxymethylphenylboronic acid. Background technique [0002] 4-Hydroxymethylphenylboronic acid is an important liquid crystal intermediate, pharmaceutical intermediate, chemical raw material intermediate, polymer intermediate and antioxidant. In recent years, with the rapid development of liquid crystal, pharmaceutical and other industries, the demand for 4-hydroxymethylphenylboronic acid has also greatly increased. [0003] At present, 4-hydroxymethylphenylboronic acid mainly has the following several synthetic routes: [0004] The first is that 4-bromobenzaldehyde and ethylene glycol carry out acetalization reaction under acid catalyst conditions to obtain 4-bromobenzaldehyde ethylene glycol acetal shown in formula II, and further obtain 4-[ 2-(1,3-dioxa)cyclopentyl]phenylboronic acid is hydrolyzed to obtain 4-formylphenylboronic acid rep...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/025Y02P20/55
Inventor 岳刚王志强丁秋月禹凯王利民陈少华张力关登仕王丽亚
Owner 宁夏中星显示材料有限公司
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