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Synthesis method and application of 2, 2, 2 (4-bromophenyl)-2-hydroxyacetic acid

A synthesis method and bromophenyl technology are applied in the field of synthesis of bromodifen intermediates, which can solve the problems of low utilization rate of glyoxylic acid, low product yield and the like, and achieve safe and controllable reaction system, high purity of finished products, and high reaction efficiency. mild conditions

Active Publication Date: 2021-12-24
JIANGSU HEBEN BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The purpose of the present invention is to provide a new method for synthesizing 2,2,2(4-bromophenyl)-2-hydroxyacetic acid, which solves the problems of low product yield and low utilization rate of glyoxylic acid

Method used

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  • Synthesis method and application of 2, 2, 2 (4-bromophenyl)-2-hydroxyacetic acid
  • Synthesis method and application of 2, 2, 2 (4-bromophenyl)-2-hydroxyacetic acid
  • Synthesis method and application of 2, 2, 2 (4-bromophenyl)-2-hydroxyacetic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] 1) Add 167g of 30% NaOH to the reaction kettle, add 247g of 30% glyoxylic acid dropwise at -5-0°C, finish the dropwise addition for 1-2h, keep warm for 1-2h, the reaction is over, add 149g of bromobenzene, and heat up the reaction 6-8h to bromobenzene≤1%, the intermediate I was prepared;

[0052] 2) Intermediate I was adjusted to pH=7-8 with concentrated hydrochloric acid, dehydrated to 120°C under negative pressure, added 100g of toluene, refluxed with water until the water in the kettle was ≤0.1%, removed the toluene under negative pressure, and added 200g of dimethyl sulfoxide , 0.82g N-hydroxyphthalimide, 1.25g cobalt acetate with four crystal waters, at 0.3-0.6MPa, 80-120℃, slowly feed oxygen, and maintain the pressure in the kettle at 0.3-0.6MPa Between, within 4-6h, the pressure in the kettle drops ≤0.01MPa, and the intermediate II is obtained;

[0053] 3) Lower the temperature of intermediate II to 10-20°C, add 165g of bromobenzene and 75.6g of sodium methoxide...

Embodiment 2

[0057] 1) Add 187g of 30% NaOH to the reaction kettle and add 247g of 30% glyoxylic acid dropwise at -5-0°C. After 1-2 hours of dropping, keep warm for 1-2 hours. When the reaction is over, add 152g of bromobenzene and heat up the reaction 6-8h to bromobenzene≤1%, the intermediate I was prepared;

[0058] 2) Intermediate I was adjusted to pH=7-8 with concentrated hydrochloric acid, dehydrated to 120°C under negative pressure, added 100g of toluene, refluxed with water until the water in the kettle was ≤0.1%, removed the toluene under negative pressure, and added quantitatively 200g of dimethylmethylene Sulfone, 1.63g N-hydroxyphthalimide, 2.5g cobalt acetate with four crystal waters, at 0.3-0.6MPa, 80-120°C, slowly feed oxygen, and maintain the pressure in the kettle at 0.3-0.6 Between MPa, within 4-6 hours, the pressure in the kettle drops ≤ 0.01MPa, and intermediate II is produced;

[0059] 3) Lower the temperature of Intermediate II to 10-20°C, add 188.5g of bromobenzene and...

Embodiment 3

[0063] 1) Add 233.5g of 30% KOH to the reaction kettle and add 247g of 30% glyoxylic acid dropwise at -5-0°C. After 1-2 hours of dropping, keep warm for 1-2 hours. When the reaction is over, add 150g of bromobenzene and heat up React for 6-8h until bromobenzene≤1%, and intermediate Ⅰ is obtained;

[0064] 2) Intermediate I was adjusted to pH=7-8 with concentrated hydrochloric acid, dehydrated to 120°C under negative pressure, added 100g of toluene, refluxed with water until the water in the kettle was ≤0.1%, removed the toluene under negative pressure, and added quantitatively 200g of dimethylmethylene Sulfone, 1.1g N-hydroxyphthalimide, 1.5g cobalt acetate with four crystal waters, under the conditions of 0.3-0.6MPa, 80-120℃, slowly feed oxygen, and maintain the pressure in the kettle at 0.3-0.6 Between MPa, within 4-6 hours, the pressure in the kettle drops ≤ 0.01MPa, and intermediate II is produced;

[0065] 3) Lower the temperature of Intermediate II to 10-20°C, add 170.5...

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Abstract

The invention provides a synthesis method and application of 2, 2-2 (4-bromophenyl)-2-hydroxyacetic acid, and the synthesis method is characterized in that under the catalysis of an alkaline condition, 2, 2-2 (4-bromophenyl)-2-hydroxyacetic acid bromobenzene and glyoxylic acid are subjected to addition, oxidation, secondary addition and acidification to prepare a bromopropylate key intermediate 2, 2-2 (4-bromophenyl)-2-hydroxyacetic acid. The 2, 2-2 (4-bromophenyl)-2-glycolic acid prepared by the preparation method disclosed by the invention is relatively high in yield, the utilization rate of glyoxylic acid is relatively high, and the 2, 2-2 (4-bromophenyl)-2-glycolic acid prepared by the preparation method disclosed by the invention is used for preparing bromopropylate.

Description

technical field [0001] The present invention relates to a kind of synthetic method and application of bromofen intermediate Background technique [0002] 2,2,2(4-bromophenyl)-2-hydroxyacetic acid is esterified with isopropanol to obtain bromofen, and 2,2,2(4-bromophenyl)-2-hydroxyacetic acid is a synthetic bromofen As an intermediate of ester, there are generally two routes for the synthesis of bromofen in industrial production: [0003] 1. Using p-bromobenzaldehyde as a raw material, bromofen was prepared through benzoin condensation, oxidation, rearrangement and esterification. [0004] [0005] The raw material p-bromobenzaldehyde required by this route is relatively difficult to obtain, the yield in the preparation process is not high, and manganese dioxide solid waste is produced, and the industrial production cost is relatively high. [0006] 2. Prepare bromofen by condensation, esterification and oxidation of glyoxylic acid and bromobenzene. [0007] [0008]...

Claims

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Application Information

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IPC IPC(8): C07C51/367C07C51/41C07C51/02C07C59/56C07C51/373C07C59/88C07C67/08C07C69/732
CPCC07C51/367C07C51/412C07C51/02C07C51/41C07C51/373C07C67/08C07C59/56C07C59/88C07C69/732
Inventor 冯魏贾利华陈华陈石秀徐鹏鹏邢燕
Owner JIANGSU HEBEN BIOCHEM
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