Method for preparing 4-chlorophenylcyclopropyl methyl ketone

A technology of chlorophenyl cyclopropyl methyl ketone and cyclopropyl methyl bromide is applied in the field of preparation of pesticide intermediates, can solve the problems of high production cost, high price, cannot meet industrial production requirements and the like, and achieves low cost and method. simple effect

Active Publication Date: 2009-03-25
JIANGSU INST OF ECOMONES +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method is simple in route and easy to operate, due to the high price of raw material cyclopropylacetic acid (1000 yuan / kg), the production cost is too high to meet the requirements of industrialized production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Preparation of cyclopropylacetonitrile:

[0015] Add 21.6g of cyclopropylmethanol (0.3mol), 84g of triphenylphosphine (0.3mol) and 200ml of diethyl ether in a reaction flask equipped with a stirrer, a thermometer, and a constant pressure dropping funnel, and cool to - At 10°C, 23.52g of liquid bromine (0.15mol) was added dropwise, and after 30 minutes of addition, the temperature was naturally raised to 15-25°C for 4 hours. After the reaction was completed, the reaction solution was suction-filtered, and the filtrate was dried and concentrated to obtain 33 g of cyclopropyl bromide.

[0016] Add 16.5g of NaCN (0.337mol), 1g of benzyltriphenylammonium chloride and 32ml of hot water in a reaction flask equipped with a stirrer, a thermometer, and a constant pressure dropping funnel, stir until fully dissolved, and cool to 0°C, add 32.3g of cyclopropylbromomethane (0.239mol) obtained by the above method dropwise, and finish adding in 30 minutes, continue to react at 0°C for...

Embodiment 2～ Embodiment 6

[0021] The preparation method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 1.

[0022] Table 1

[0023] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Magnesium metal 1.68g,

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Abstract

The invention discloses a preparing method of 4-chlorophenyl cyclopropyl ketone, which comprises the following steps: 1) magnesium metal is added into an organic solvent of ether or tetrahydrofuran, para chlorobromobenzene solution with the same volume of the solvent is dripped, the mixed solution is heated to the reflux temperature of the solvent so as to lead the reaction system to have a reaction of generating Grignard reagent and reflux reaction is carried out for 1 to 2h; and 2) the system obtained from the step 1) is cooled to minus 5 to 0 DEG C, then cyclopropane acetonitrile solution with the same volume of the solvent is dripped into the system, after that, the new system is heated to the same reflux temperature with the solvent so as to lead the reaction system to have a reaction of generating the 4-chlorophenyl cyclopropyl ketone, and flux reaction is carried out for 1 to 2h; and a finished product of 4-chlorophenyl cyclopropyl ketone is obtained after post treatment. The method has the advantages of simpleness, low cost and being suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a pesticide intermediate, in particular to a preparation method of 4-chlorophenyl cyclopropyl methyl ketone. Background technique [0002] 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone is the key intermediate for the preparation of the fungicide cyproconazole, and 4-chlorophenylcyclopropylmethyl ketone is the key intermediate for the preparation of 1-(4 -Chlorophenyl)-2-cyclopropyl-1-propanone is an important intermediate. [0003] U.S. Patent No. 4,664,696 discloses a synthetic method of 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone, which first reacts the magnesium compound of p-chlorobenzaldehyde and chloropropene, and the product is used again Cyclopropanation of dibromomethane followed by oxidation with oxalyl chloride in the presence of triethylamine affords 4-chlorophenylcyclopropylmethyl ketone. The method has long synthesis steps, many unit operations, and harsh conditions, and the product yield and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/333C07C45/00
Inventor 孔繁蕾孙永辉史志兵
Owner JIANGSU INST OF ECOMONES
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