Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

2-chloro-4-fluorobenzoic acid and preparation method thereof

A technology of fluorobenzoic acid and chlorobenzoic acid, which is applied in the field of biomedicine, can solve the problems of high toxicity of dichromate, low product yield, environmental pollution, etc., and achieve the improvement of purity and yield, low catalyst cost, and control process conditional effect

Inactive Publication Date: 2016-07-06
叶芳
View PDF4 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the traditional synthesis process of 2-chloro-4-fluorobenzoic acid in China, dichromate is usually used as an oxidant, but dichromate is very toxic, pollutes the environment very seriously, and the product yield is very low

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Preparation of N,N-bis(trimethylsilyl)ethoxymethyl-3-chloroaniline

[0027] Add 1 mol of m-chloroaniline, 2 mol of potassium carbonate, 0.02 mol of potassium iodide, 10 mol of ionic liquid and 50 mol of deionized water into a four-neck flask, heat the reaction solution to 100°C after dissolving, and add 2-(trimethylsilyl)ethoxymethyl dropwise Base chloride 0.36mol, after the dropwise addition, react for 1h, cool to room temperature, add 3L of ice water while stirring at 1000 rpm, cool down to 2-3°C, continue stirring, precipitate solid, stand still, and suction filter, The filter cake was washed with 5×100 mL deionized water, and then dried to obtain N,N-bis(trimethylsilyl)ethoxymethyl-3-chloroaniline with a yield of 90.5%;

[0028] (2) Preparation of 4-bis(trimethylsilyl)ethoxymethylamino-2-chlorobenzaldehyde

[0029] Add 0.65mol of N,N-bis(trimethylsilyl)ethoxymethyl-3-chloroaniline, 5mol of ionic liquid and 50mol of water to dissolve in a 500mL four-neck flask, ...

Embodiment 2

[0035] (1) Preparation of N,N-bis(trimethylsilyl)ethoxymethyl-3-chloroaniline

[0036] Add 5 mol of m-chloroaniline, 5 mol of potassium carbonate, 0.05 mol of potassium iodide, 10 mol of ionic liquid and 50 mol of deionized water into a four-neck flask, heat the reaction solution to 100°C after dissolving, and add 2-(trimethylsilyl)ethoxymethyl dropwise Base chloride 2mol, after the dropwise addition, react for 3h, cool to room temperature, add 3L of ice water while stirring at 2000 rpm, cool down to 2-3°C, continue stirring, precipitate solid, stand still, suction filter, filter The cake was washed with 5×100 mL deionized water, and then dried to obtain N,N-bis(trimethylsilyl)ethoxymethyl-3-chloroaniline with a yield of 92.5%;

[0037] (2) Preparation of 4-bis(trimethylsilyl)ethoxymethylamino-2-chlorobenzaldehyde

[0038] Add 1 mol of N,N-bis(trimethylsilyl)ethoxymethyl-3-chloroaniline, 5 mol of ionic liquid and 50 mol of water into a 500 mL four-necked flask, add titanium t...

Embodiment 3

[0044] (1) Preparation of N,N-bis(trimethylsilyl)ethoxymethyl-3-chloroaniline

[0045] Add 2 mol of m-chloroaniline, 3 mol of potassium carbonate, 0.03 mol of potassium iodide, 10 mol of ionic liquid and 50 mol of deionized water into a four-neck flask, heat the reaction solution to 100°C after dissolving, and add 2-(trimethylsilyl)ethoxymethyl dropwise Base chloride 0.38mol, after the dropwise addition, react for 1.5h, cool to room temperature, add 3L of ice water while stirring at 1500 rpm, cool down to 2-3°C, continue stirring, precipitate solid, stand still, and suction filter , the filter cake was washed with 5×100mL deionized water, and then dried to obtain N,N-bis(trimethylsilyl)ethoxymethyl-3-chloroaniline with a yield of 93.3%;

[0046] (2) Preparation of 4-bis(trimethylsilyl)ethoxymethylamino-2-chlorobenzaldehyde

[0047] Add 0.7mol of N,N-bis(trimethylsilyl)ethoxymethyl-3-chloroaniline, 5mol of ionic liquid and 50mol of water to dissolve in a 500mL four-neck flask, a...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses 2-chloro-4-fluorobenzoic acid and a preparation method thereof. In the method, m-chloroaniline is used as a raw material, and the protection of the amino group is realized through 2-(trimethylsilyl)ethoxymethyl chloride successively, and the Vilsmeier-Haack reaction is realized. Formylation, then oxidation to carboxylic acid, hydrogenation to reduce the nitro group, and then fluorination reaction to prepare 2-chloro-4-fluorobenzoic acid. The pesticide intermediate 2-chloro-4-fluorobenzoic acid provided by the present invention is simple to prepare, suitable for mass production, and uses cheap m-chloroaniline as a raw material, and uses a substance with low volatility and low toxicity as a reaction during the preparation process. Medium, reasonably control the type and amount of catalyst and oxidant, so that the yield of the product can reach more than 85%.

Description

Technical field: [0001] The invention relates to the technical field of biomedicine, in particular to a pharmaceutical intermediate 2-chloro-4fluorobenzoic acid and a synthesis method thereof. Background technique: [0002] 2-Chloro-4fluorobenzoic acid is an important drug and pesticide intermediate, which can also be used in liquid crystal materials, and has the advantages of high value and good market prospects. From the perspective of physiology, compared with general inorganic drugs, fluorine-containing drugs have better biopenetration and better selectivity to target organs, and the dosage usually used is greatly reduced. Therefore, fluorine is widely used in the preparation of fluorine-containing pharmaceuticals with special curative effects. Moreover, fluorine-containing compounds have the characteristics of less pollution to the environment, less dosage, high efficacy, low toxicity, less side effects, and strong metabolism. Therefore, the development of fluorine-con...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/363C07C63/70C07F7/08C07C227/12C07C229/60
CPCC07C51/363C07C63/70C07C227/12C07F7/081C07F7/083C07C229/60
Inventor 叶芳
Owner 叶芳
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com