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Preparation method of 5-bromo-2-chlorobenzoic acid

A technology of chlorobenzoic acid and chlorotrichlorotoluene, which is applied in the preparation of carboxylate, the preparation of organic compounds, the preparation of halogenated hydrocarbons, etc., can solve problems such as unfavorable environmental protection, multi-strong acid waste water, etc. The effect of low cost, omitting intermediate purification and post-processing

Pending Publication Date: 2020-09-04
吴赣药业(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This reaction requires two-step synthesis, and strong acids such as sulfuric acid are used in the hydrolysis reaction, which produces more strongly acidic wastewater, which is not conducive to environmental protection

Method used

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Examples

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Comparison scheme
Effect test

preparation example Construction

[0018] A preparation method of 5-bromo-2-chlorobenzoic acid is characterized in that it comprises the steps of: taking 2-chlorotrichloromethylbenzene as raw material and brominating reagent to react under the catalysis of the first catalyst to generate 2-chlorobenzoic acid -5-bromotrichlorotoluene, then add water therein, hydrolysis catalyst, after aftertreatment, purification makes 5-bromo-2-chlorobenzoic acid; Described first catalyst is ferric bromide, ferrous bromide, Copper bromide, (ferrocenemethyl)trimethylammonium bromide, and brominated ferrocene are compounded.

[0019] Preferably, the bromination reagent is at least one of bromine, N-bromoimide, and tetrabutylammonium bromide.

[0020] Preferably, the first catalyst is ferric bromide, ferrous bromide, copper bromide, (ferrocenemethyl) trimethylammonium bromide, brominated ferrocene in a mass ratio of 1:1:( 0.1-0.3):(0.3-0.6):0.1 mixed.

[0021] Preferably, the hydrolysis catalyst is at least one of sulfamic acid, ...

Embodiment 1

[0030] Embodiment 1 provides a kind of preparation method of 5-bromo-2-chlorobenzoic acid, it is characterized in that, comprises the steps: take 2-chlorobenzotrichlorotoluene as raw material and bromination reagent to react under the catalysis of the first catalyst, Generate 2-chloro-5-bromobenzoic acid, then add water therein, hydrolyze the catalyst, and after post-treatment, purify to obtain 5-bromo-2-chlorobenzoic acid; the first catalyst is ferric bromide, bromine Ferrous chloride, copper bromide, (ferrocenemethyl)trimethylammonium bromide, and brominated ferrocene are compounded.

[0031] The bromination reagent is bromine; the first catalyst is ferric bromide, ferrous bromide, copper bromide, (ferrocenemethyl) trimethyl ammonium bromide, brominated ferrocene by mass ratio It is formed by mixing 1:1:0.1:0.3:0.1; the hydrolysis catalyst is sulfamic acid.

[0032] The molar ratio of the 2-chlorobenzotrichloride, the brominating reagent, the first catalyst, water, and the ...

Embodiment 2

[0036] Embodiment 2 provides a kind of preparation method of 5-bromo-2-chlorobenzoic acid, and it is substantially the same as embodiment 1, and difference is, described first catalyst is ferric bromide, ferrous bromide, cupric bromide, (Ferrocenemethyl)trimethylammonium bromide and ferrocene bromide are mixed in a mass ratio of 1:1:0.15:0.4:0.1; the 2-chlorobenzotrichloride, brominating reagent, and The molar ratio of catalyst, water and hydrolysis catalyst is 1:1:0.25:70:3.5.

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Abstract

The invention relates to a preparation method of 5-bromo-2-chlorobenzoic acid, which is characterized by comprising the following steps: reacting 2-chlorobenzotrichloride used as a raw material with abromination reagent under the catalytic action of a first catalyst to generate 2-chloro-5-bromobenzotrichloride, adding water and a hydrolysis catalyst into the 2-chloro-5-bromobenzotrichloride, andcarrying out after-treatment and purification to obtain 5-bromo-2-chlorobenzoic acid, wherein the first catalyst is prepared by compounding iron bromide, ferrous bromide, copper bromide, (ferrocene methyl) trimethyl ammonium bromide and brominated ferrocene. The invention further discloses the 5-bromine-2-chlorobenzoic acid prepared according to the preparation method of the 5-bromine-2-chlorobenzoic acid. According to the preparation method of 5-bromine-2-chlorobenzoic acid disclosed by the invention, the traditional preparation process conditions are optimized and innovated, so that the product purity, the reaction conversion rate and the production efficiency are effectively improved, the preparation cost is low, the environmental pressure is low, the synthesis route is short, the operation is simple and feasible, the emission of three wastes is reduced, and the reaction yield is high.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of 5-bromo-2-chlorobenzoic acid. Background technique [0002] SGLT-2 inhibitors are a new generation of diabetes drugs. They control blood sugar by inhibiting the reabsorption of glucose in the kidneys. The mechanism of action is unique and does not depend on the abnormality of β cells or the degree of insulin resistance, and the effect will not vary with The failure of β-cell function or the decline of severe insulin resistance will not cause adverse reactions caused by traditional drugs, and has a variety of clinical advantages, especially in clinically showing the advantage of reducing cardiovascular risk. 5-bromo-2-chlorobenzoic acid is a common key intermediate for the synthesis of new antidiabetic drugs SGLT-2 inhibitors, therefore, it is particularly important to seek a suitable preparation method for 5-bromo-2-chlorobenzoic acid. [0003] The...

Claims

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Application Information

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IPC IPC(8): C07C63/70C07C51/093C07C51/42
CPCC07C63/70C07C51/093C07C51/42C07C17/12C07C2531/30C07C2527/24
Inventor 钱炜雯刘永超
Owner 吴赣药业(苏州)有限公司
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