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Synthetic method of 1-halo-1-acetyl cyclopropane

A technology based on cyclopropane and a synthesis method, which is applied in the field of synthesis of pharmaceutical and pesticide intermediates, can solve the problems of harsh reaction conditions, complicated operation, long reaction time, etc., and achieves a short time consumption, harsh reaction conditions, and mild conditions. Effect

Inactive Publication Date: 2018-03-06
XIAN MODERN CHEM RES INST
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  • Abstract
  • Description
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Problems solved by technology

[0003] The method (Lutz Fitjer, Synthesis, 1977, 189-191) of the synthesis 1-halo-1-acetylcyclopropane compound reported in the current literature is under the effect of potassium fluoride, with diethylene glycol as a solvent, The reaction temperature is 110°C~130°C. While adding the raw material 3,5-dihalo-2-pentanone compound dropwise, the product is distilled out under low pressure (-30torr~-10torr). The reaction conditions are harsh and the operation is complicated. , has higher requirements on equipment, especially after batch amplification, the amplification effect is obvious, and the reaction takes a long time, which is not suitable for industrial production; in addition, after the reaction is stopped, there are many impurities in the remaining diethylene glycol reaction liquid, which is not conducive to solvent recovery

Method used

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  • Synthetic method of 1-halo-1-acetyl cyclopropane
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  • Synthetic method of 1-halo-1-acetyl cyclopropane

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Effect test

Embodiment 1

[0015] At 0°C, 50 mL of dichloromethane, 6 g (0.15 mol) of sodium hydroxide and 0.09 g (4×10 -4 mol) benzyltriethylammonium chloride, and then 15.5 grams (0.1 mol) of 3,5-dichloro-2-pentanone was added dropwise. After the dropwise addition, the temperature was raised, refluxed for 0.5 hours, and cooled to room temperature. The reaction solution was washed twice with water, separated, and the organic phase was dried over anhydrous sodium sulfate and evaporated to dryness to obtain 12 g of a light yellow transparent liquid. It was confirmed to be 1-chloro-1-acetylcyclopropane by NMR analysis, with a yield of 96.5% and a purity of 95.3%. 1 H NMR (CDCl 3 ,500MHz, δ / ppm):2.46(s,3H),1.64(dd,J=8.5,5.0Hz,2H),1.35(dd,J=8.5,5.0Hz,2H).

Embodiment 2

[0017] At 0°C, 50 mL of dichloromethane, 6 g (0.15 mol) of sodium hydroxide and 0.09 g (4×10 -4 mol) benzyltriethylammonium chloride, and then 20 g (0.1 mol) of 3-chloro-5-bromo-2-pentanone was added dropwise. After the dropwise addition, the temperature was raised, refluxed for 0.5 hours, and then cooled to room temperature. The reaction solution was washed twice with water and separated. The organic phase was dried over anhydrous sodium sulfate and evaporated to dryness to obtain 11.9 g of a light yellow transparent liquid. It was confirmed to be 1-chloro-1-acetylcyclopropane by NMR analysis, with a yield of 98% and a purity of 97.5%.

Embodiment 3

[0019] At 0°C, 50 mL of toluene, 8 g (0.2 mol) of sodium hydroxide and 0.09 g (4×10 - 4 mol) benzyltriethylammonium chloride, and then 20 g (0.1 mol) of 3-bromo-5-chloro-2-pentanone was added dropwise. After the dropwise addition, the temperature was raised to 100° C., reacted for 2 hours, and then cooled to room temperature. The reaction solution was washed twice with water and separated. The organic phase was dried over anhydrous sodium sulfate and evaporated to dryness to obtain 15.9 g of a light yellow transparent liquid. It was confirmed to be 1-bromo-1-acetylcyclopropane by NMR analysis, with a yield of 84% and a purity of 86%. 1 HNMR (CDCl 3 ,500MHz,δ / ppm):2.47(s,3H),1.68-1.71(m,2H),1.41-1.44(m,2H).

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Abstract

The invention discloses a synthetic method of 1-halo-1-acetyl cyclopropane. The synthetic method comprises the step of preparing a 1-halo-1-acetyl cyclopropane compound by taking 3,5-dihalo-pentanoneas a raw material and taking benzyl trimethyl ammonium chloride as a phase transfer catalyst under the action of alkali. The method disclosed by the invention is simple to operate, quick to react andhigh in yield, and solves the problem of quickly and efficiently synthesizing the 1-halo-1-acetyl cyclopropane compound. The synthetic method disclosed by the invention is primarily used for synthesizing organic molecules containing cyclopropane structural units.

Description

technical field [0001] The invention belongs to the field of synthesis of pharmaceutical and pesticide intermediates, in particular to a synthesis method of 1-halogenated-1-acetylcyclopropane compound. Background technique [0002] 1-halo-1-acetylcyclopropane compounds are pharmaceutical and pesticide intermediates with broad application prospects, among which 1-acetyl-1-chlorocyclopropane is a new broad-spectrum triazolethione fungicide propylthio An important intermediate required in the synthesis of cloconazole (US4913727; US6201128). 1-Halo-1-acetylcyclopropane compounds are usually prepared from 3,5-dihalo-2-pentanone compounds as raw materials. [0003] The method (Lutz Fitjer, Synthesis, 1977, 189-191) of the synthesis 1-halo-1-acetylcyclopropane compound reported in the current literature is under the effect of potassium fluoride, with diethylene glycol as a solvent, The reaction temperature is 110°C~130°C. While adding the raw material 3,5-dihalo-2-pentanone compo...

Claims

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Application Information

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IPC IPC(8): C07C49/327C07C45/65
CPCC07C45/65C07C49/327
Inventor 李秉擘王月梅王威宁斌科杨翠凤卫天琪徐泽刚张媛媛
Owner XIAN MODERN CHEM RES INST
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