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Method for preparing cyclopropyl o-fluobenzyl ketone

A technology of o-fluorobenzyl ketone and cyclopropyl, applied in the direction of condensation to prepare carbonyl compounds, organic chemistry, etc., to achieve the effect of good safety and cost reduction

Active Publication Date: 2011-05-04
ZHEJIANG HUABANG MEDICAL & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The technical problem to be solved by the present invention is to provide a synthetic method of cyclopropyl o-fluorobenzyl ketone, so as to solve many deficiencies in existing methods

Method used

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  • Method for preparing cyclopropyl o-fluobenzyl ketone
  • Method for preparing cyclopropyl o-fluobenzyl ketone
  • Method for preparing cyclopropyl o-fluobenzyl ketone

Examples

Experimental program
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Effect test

Embodiment 1

[0040] (1) Add 15.7g zinc powder (1.6eq.), anhydrous LiCl 9.5g (1.5eq.) into a 500ml dry four-necked reaction flask, add 50ml tetrahydrofuran, 1.4g dibromoethane (5% mol), Heated to reflux for 10 min under nitrogen protection. After cooling slightly, 1.5 ml (1% mol) of 1.0 M TMS-Cl in tetrahydrofuran was added, and heated to reflux again for 10 min. Cool to 20°C, start dropwise adding 21.7g o-fluorobenzyl chloride in 250ml tetrahydrofuran solution, during the dropwise addition, use ice water to control the reaction temperature not to exceed 25°C, dropwise is completed in about 2 hours, continue to keep stirring for 1.5 hours, and filter to obtain 0.5 M O-fluorochlorobenzyl zinc reagent. The yield is nearly quantitative.

[0041] (2) Under the protection of nitrogen, 1.0g of anhydrous CuCl 2 (5% mol) and 0.64 g of anhydrous LiCl (10% mol) were added to a 500 ml four-necked reaction flask, 75 ml of tetrahydrofuran was added, and stirred for 30 min to obtain a lithium tetrachl...

Embodiment 2

[0043] (1) Add 15.7g zinc powder (1.6eq.), anhydrous LiCl 9.5g (1.5eq.) into a 500ml dry four-necked reaction flask, add 50ml tetrahydrofuran, 1.4g dibromoethane (5% mol), Heated to reflux for 10 min under nitrogen protection. After cooling slightly, 1.5 ml (1% mol) of 1.0 M TMS-Cl in tetrahydrofuran was added, and heated to reflux again for 10 min. Cool to 20°C, start dropwise adding 21.7g o-fluorobenzyl chloride in 250ml tetrahydrofuran solution, during the dropwise addition, use ice water to control the reaction temperature not to exceed 25°C, dropwise is completed in about 2 hours, continue to keep stirring for 1.5 hours, and filter to obtain 0.5 M O-fluorochlorobenzyl zinc reagent. The yield is nearly quantitative.

[0044] (2) First prepare 21.7 g of zinc reagent solution of o-fluorobenzyl chloride according to experiment (1), add 23.5 g (1.5 eq.) of cyclopropylformyl chloride to this solution, and heat to reflux overnight under nitrogen protection. Cool to room tempe...

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Abstract

The invention relates to a method for preparing cyclopropyl o-fluobenzyl ketone. The method comprises the following steps of: (1) carrying out metalized treatment on o-fluo benzyl halide by using tetrahydrofuran or methyl tetrahydrofuran as a reaction medium to obtain a metal reagent of the o-fluo benzyl halide, wherein the metal is the combination of Zn, or Zn / LiCl; and (2) reacting the obtained metalized reagent of the o-fluo benzyl halide with cyclopropyl formyl chloride to generate cyclopropyl o-fluobenzyl ketone, wherein the reaction also can be carried out in the presence of transition metal ions, and the reagent of the transition metal ions is palladium acetate or palladium chloride or triphenyl phosphine palladium or anhydrous nickel chloride or triphenyl nickel chloride phosphine or ferric trichloride or acetyl acetone iron or copper chloride or cuprous chloride or lithium cuprate tetrachloride. In the metalized method, the tetrahydrofuran or the methyl tetrahydrofuran is used as the reaction medium, thus the method has higher yield and better safety compared with a traditional method; and cyclopropyl formyl chloride which has low price and is easy to obtain is used as a raw material to react with the metalized o-fluo benzyl halide, thus the cost is greatly reduced.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of cyclopropyl o-fluorobenzyl ketone, belonging to the field of organic chemistry. Background technique [0002] The compound cyclopropyl o-fluorobenzyl ketone is an intermediate of a new generation of platelet inhibitor prasugrel. The CAS registration number of the compound is 150322-73-9, and the specific structure is shown in the figure below: [0003] [0004] Regarding the synthesis method of cyclopropyl-o-fluorobenzyl ketone, only a few patents have publicly reported its synthesis method. [0005] In 1993, Canadian patent CA2077695 reported a kind of o-fluorobenzyl bromide as the starting material, first reacted with magnesium chips in ether to produce Grignard reagent, and then reacted with cyclopropylcarbonitrile to obtain cyclopropyl o-fluorobenzyl ketone Synthetic method (as shown in the figure below). [0006] [0007] The method uses ...

Claims

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Application Information

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IPC IPC(8): C07C49/567C07C45/45
Inventor 洪道送刘新科伍小唐
Owner ZHEJIANG HUABANG MEDICAL & CHEM
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