Unlock instant, AI-driven research and patent intelligence for your innovation.

Practical synthetic method of 2-halogen-1-(4-bromine-3-fluorophenyl) butanone

A synthesis method and fluorophenyl technology are applied in the practical synthesis field of 2-halo-1-ethanone, can solve the problems of long synthesis route, troublesome post-processing, complicated operation, etc., and achieve low cost of raw materials, operation and post-processing. The effect of convenience and simple ingredients

Active Publication Date: 2012-03-14
SUZHOU KANGRUN PHARMA
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention develops a synthesis process for obtaining 2-halo-1-(4-bromo-3-fluorophenyl)ethanone by α-halogenation, avoiding the relatively long synthesis route, complicated operation, troublesome post-processing, and difficulty in scaling up, etc. shortcoming

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

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Practical synthetic method of 2-halogen-1-(4-bromine-3-fluorophenyl) butanone
  • Practical synthetic method of 2-halogen-1-(4-bromine-3-fluorophenyl) butanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0013] Below in conjunction with embodiment the present invention is described in further detail.

[0014] Implementation column 1 Synthesis of 2-chloro-1-(4-bromo-3-fluorophenyl)ethanone

[0015] 4-Bromo-3-fluoroiodobenzene (33g, 0.11mol, purchased from Hebei Meixing Chemical Co., Ltd.) was dissolved in 17ml of anhydrous tetrahydrofuran, under nitrogen protection, cooled to 0°C, and slowly added isopropylmagnesium bromide 0.11 mol dissolved in tetrahydrofuran (55 ml, 2.0M), after the dropwise reaction was stirred at 0°C for 1 hour. Cool down to -70°C, slowly add dropwise a solution of 2-chloro-N-methoxy-N-methylacetamide (13.6g, 0.099mol, Shanghai Baoman Biotechnology Co., Ltd.) dissolved in 15ml of anhydrous tetrahydrofuran, Keep the temperature below -60°C. After the dropwise reaction was stirred at room temperature for 1 hour. Saturated ammonium chloride solution quenched the reaction, concentrated to remove most of THF, added water and ethyl acetate to separate laye...

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 relates to a practical synthetic method of 2-halogen-1-(4-bromine-3-fluorophenyl) butanone. According to the invention, alpha is halogenated to obtain the 2-halogen-1-(4-bromine-3-fluorophenyl) butanone in such a way that 4-bromo-3-fluoroiodobenzene is adopted as raw material to be treated by using a Grignard reagent and directly reacts with Weinreb amide corresponding to halogenated acetic acid so as to obtain the 2-halogen-1-(4-bromine-3-fluorophenyl) butanone. According to the invention, the defects of comparatively longer synthetic route, complicatedness in operation, difficulties in post treatment, uneasiness for amplifying and the like in the traditional method are solved; a synthetic method with simple synthetic route, reasonability in selecting the process, low raw material cost, simplicity and easiness in obtaining the raw material, convenience in operation and post treatment, high total yield, easiness for amplifying and capability of carrying out large-scale production is provided; and in the synthetic method, the 4-bromo-3-fluoroiodobenzene is adopted as raw material and alpha is halogenated to obtain the 2-halogen-1-(4-bromine-3-fluorophenyl) butanone.

Description

technical field [0001] The invention relates to a practical synthesis method of 2-halo-1-(4-bromo-3-fluorophenyl)ethanone. Background technique [0002] 2-Halo-1-(4-bromo-3-fluorophenyl)ethanone is a very important intermediate. It can be used as a raw material to synthesize many natural Or non-natural compounds. Because this compound exhibits such superior reaction characteristics, medicinal chemists can modify it to obtain different compounds, so as to conduct SAR research and screen out some highly effective drug candidate molecules, so It has aroused widespread concern in the medicinal chemistry community. A typical example is that starting from 2-bromo-1-(4-bromo-3-fluorophenyl)ethanone, medicinal chemists have synthesized molecules with very high FAAH inhibitory activity (WO2009151991 ). [0003] The synthesis of 2-halo-1-(4-bromo-3-fluorophenyl)ethanone, the current method mainly starts from 4-bromo-3-fluorotoluene, first obtains 4-bromo-3-fluorotoluene by oxidation...

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
IPC IPC(8): C07C49/80C07C45/00
Inventor 徐卫良储玉平左兵徐炜政
Owner SUZHOU KANGRUN PHARMA