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Synthesis method of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone

A synthetic method and cyclopropyl technology, applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of low product purity, long reaction route, and many side reactions, and achieve high purity, The effect of high yield and reaction conversion rate and low production cost

Inactive Publication Date: 2018-09-14
SHANDONG WEIFANG RAINBOW CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] CN101857576A takes p-chlorobenzyl chloride and cyclopropyl methyl ketone as raw materials, and the product yield is 80-90%, because the reaction route is long and there are many side reactions, so the product purity is lower, below 80%, so it is necessary to treat crude The product is purified by complicated column chromatography, which is cumbersome and causes a large loss of the product

Method used

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  • Synthesis method of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone
  • Synthesis method of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone
  • Synthesis method of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Add excess magnesium chips and 1000mL tetrahydrofuran to a dry round-bottomed flask, then dropwise add 1-chloroethylcyclopropane (1mol), the resulting mixture is stirred and reacted at room temperature for 3 hours, and filtered after reaction to remove magnesium chips to obtain Tetrahydrofuran solution (1mol / L) of the compound of formula (II); the reaction formula is as follows:

[0029]

Embodiment 2

[0031] Add 4-chlorobenzoyl chloride (0.10mol), catalyst iron triacetylacetonate (0.003mol), and isopropyl ether (250mL) into the reaction flask, and add the compound of formula (II) prepared in Example 1 dropwise at 0°C. The tetrahydrofuran solution of the compound was 100mL, after dropping, the reaction was continued at this temperature for 1 hr, after the reaction, 250mL of cold water was added dropwise to the reaction solution, after the dropping, the solid was removed by filtration, the organic phase was collected, dried, concentrated and crystallized under reduced pressure to obtain 1-( 17.3 g of 4-chlorophenyl)-2-cyclopropyl-1-propanone product, the yield was 82.9% based on 4-chlorobenzoyl chloride, and the purity by HPLC was 99.1%.

Embodiment 3

[0033] Add 4-chlorobenzoyl chloride (0.10mol), catalyst iron triacetylacetonate (0.004mol), and tetrahydrofuran (250mL) into the reaction flask, and add the compound of formula (II) prepared in Example 1 dropwise at -10°C 100mL of tetrahydrofuran solution, after dropping, continue to react at this temperature for 2hr, after the reaction, add 250mL of cold water dropwise to the reaction solution, after dropping, remove the solid by filtration, collect the organic phase, dry, concentrate and crystallize under reduced pressure to obtain 1-(4 -Chlorophenyl)-2-cyclopropyl-1-propanone product 17.7g, the yield is 84.8% based on 4-chlorobenzoyl chloride, and the purity detected by HPLC is 99.2%. .

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Abstract

The invention discloses a synthesis method of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone. The method comprises the following steps: taking compounds expressed as formula (I) and formula (II) which areas shown in the description as raw materials, and carrying out cross-coupling reaction in the presence of a catalyst to prepare 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone. The synthesis method is usedfor preparing 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone by taking the compounds expressed as the formula (I) and the formula (II) as the raw materials; compared with the prior art, the synthesis method is easily available in reaction raw materials, short in synthesis route, simple in process, simple in post-treatment and low in production cost; meanwhile, the prepared 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone is high in purity being 98.5% or above and is also high in yield and reaction conversion rate; the product yield is 80-92%. (The formula is shown in the description.).

Description

technical field [0001] The invention relates to a synthesis method of 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone, in particular to a 1-(4-chlorophenyl) with simple process, low cost and high product purity )-2-cyclopropyl-1-propanone synthetic method. Background technique [0002] Cyproconazole is a triazole fungicide developed by Syngenta in 1985. It can be quickly absorbed by the vigorous growth parts of plants and is an important steroid demethylation inhibitor. 1-(4-Chlorophenyl)-2-cyclopropyl-1-propanone is a key intermediate for the preparation of cyproconazole, and its chemical structure is as follows: [0003] [0004] The prior art discloses various preparation methods of 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone, such as US4664696, CN101786948, RU2350579, CN101125807A, US4976767, CN101857576A. Most of these methods use p-chlorobenzonitrile or p-chlorobenzyl chloride as raw materials, and there are many by-products, long synthetic routes, low reaction conv...

Claims

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Application Information

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IPC IPC(8): C07C49/813C07C45/68
CPCC07C45/004C07C45/68C07C2601/02C07C49/813
Inventor 孙国庆侯永生宋健
Owner SHANDONG WEIFANG RAINBOW CHEM
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