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Preparation method of 1-(1-chlorocyclopropyl)-2-(2-chlorphenyl)ethanone and intermediate thereof

A chlorocyclopropyl, chlorophenyl technology, applied in the field of preparation of 1--2-ethanone, can solve the problems of high cost, restricting industrial development, harsh reaction conditions and the like

Inactive Publication Date: 2019-12-31
JIANGSU CHENGYANG GROP SCI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned preparation method has fewer synthesis steps and higher yield, but involves the source or preparation of organometallic reaction, noble metal catalyst and 1-chlorocyclopropylcarbonyl chloride, the reaction conditions are relatively harsh, the cost is high, and it is restricted in technology and economy. industrial development

Method used

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  • Preparation method of 1-(1-chlorocyclopropyl)-2-(2-chlorphenyl)ethanone and intermediate thereof
  • Preparation method of 1-(1-chlorocyclopropyl)-2-(2-chlorphenyl)ethanone and intermediate thereof
  • Preparation method of 1-(1-chlorocyclopropyl)-2-(2-chlorphenyl)ethanone and intermediate thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0047] Under the protection of nitrogen, 27.0g of sodium metal was added to 300mL of toluene, heated to 100°C to 110°C and stirred for 30 minutes; 185.0g of methyl 2-chlorophenylacetate and 90.0g of γ-butyl were added dropwise to the above suspension system A mixture of lactones; after the addition, continue to stir and react for 3 hours, during which the formed low boilers are evaporated from the reaction system; Stir for 30 minutes; filter with suction, wash the filter cake with 50mL of toluene, and collect the filtrate; wash the obtained filtrate with 200mL×2 water, and precipitate under reduced pressure to obtain 3-[2-(2-chlorophenyl)acetyl]-4,5 - 229.0 g of dihydrofuran-2(3H)one (II), which was in a yellow semi-solid state after standing, with a content of 93.3% by chromatographic analysis.

[0048] The above crude product was subjected to column chromatography (ethyl acetate / n-hexane 1:1) to obtain an off-white solid with a chromatographic content of 99.1%: EIMS (m / z): 2...

Embodiment 2

[0050] With reference to Example 1, 50.0 g of sodium amide was used to replace the sodium metal therein to obtain 3-[2-(2-chlorophenyl) acetyl]-4,5-dihydrofuran-2(3H) ketone (II) 225.0 g, chromatographic analysis content 90.8%.

Embodiment 3

[0052] At a temperature of 20-30°C, 30.0g of γ-butyrolactone was added dropwise to a mixture consisting of 60.0g of ethyl 2-chlorophenylacetate, 25.0g of sodium methoxide and 100mL of tetrahydrofuran, and stirring was continued for 1 hour; the obtained reaction mixture Gradually heat up to reflux state and keep reacting for 4 hours; cool to room temperature, add hydrochloric acid solution to the reaction system dropwise to about pH4, then add 150mL dichloromethane and 200mL water, continue to stir for 30 minutes and then let stand to separate; the water layer Add 50 mL of dichloromethane for extraction, combine the organic phases and wash with 100 mL of water, and desolvate under reduced pressure to obtain 70.0 g of an orange viscous residue, namely 3-[2-(2-chlorophenyl)acetyl]-4,5- Dihydrofuran-2(3H)one (II) crude product, the content of chromatographic analysis is 87.8%.

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Abstract

The invention discloses a preparation method of 1-(1-chlorocyclopropyl)-2-(2-chlorphenyl)ethanone (I) and an intermediate thereof. The preparation method of the compound (I) comprises the following steps: with 2-chlorophenylacetate and gamma-butyrolactone as raw materials, carrying out an acylation reaction under a strong alkali condition to obtain 3-[2-(2-chlorphenyl)acetyl]-4,5-dihydrofuran-2(3H)-one (II); carrying out a chlorination reaction on the compound (II) to convert the compound (II) into a corresponding chloride (III), and then subjecting the chloride (III) to a ring-opening decarboxylation reaction in hydrochloric acid to obtain 3,5-dichloro-1-(2-chlorphenyl)-2-pentanone (IV); and subjecting the compound (IV) to a cyclization reaction in the presence of an alkali to obtain 1-(1-chlorocyclopropyl)-2-(2-chlorphenyl)ethanone (I). The method has the characteristics of simple process and low raw material cost, and is convenient for large-scale development.

Description

technical field [0001] The invention belongs to the field of chemistry and chemical engineering, and relates to a preparation method of 1-(1-chlorocyclopropyl)-2-(2-chlorophenyl)ethanone, an intermediate and a preparation method of the intermediate. Background technique [0002] 1-(1-chlorocyclopropyl)-2-(2-chlorophenyl)ethanone (I) is an intermediate for preparing triazole fungicides prothioconazole and its analogues. [0003] [0004] US Patent No. 5,146,001 and US No. 5,216,006 disclose a series of preparation methods and applications of benzyl ketones including 1-(1-chlorocyclopropyl)-2-(2-chlorophenyl)ethanone (I). The preparation method uses benzyl chloride as a raw material to react with excessive zinc powder to form a corresponding zinc derivative, and further reacts with chlorocyclopropylformyl chloride under catalytic conditions to generate the described benzyl (cyclopropyl) ketone (I) . The above-mentioned preparation method has fewer synthetic steps and high...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/65C07C49/567C07D307/33C07C45/67C07C45/63C07C49/233
CPCC07C45/65C07D307/33C07C45/676C07C45/63C07C49/233C07C2601/02C07C49/567
Inventor 王晓军徐尚成朱兆勇
Owner JIANGSU CHENGYANG GROP SCI CO LTD
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