Preparation method of 4-chlorobutyroyl chloride

A technology of chlorobutyryl and butyrolactone, which is applied in the field of preparation of 4-chlorobutyryl chloride, can solve the problems of easy escape of phosgene, high reaction temperature, and no industrial operation, and achieve simple process and high yield High and low cost effect

Active Publication Date: 2010-01-13
ZHEJIANG GUOBANG PHARMA
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  • Application Information

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Problems solved by technology

[0018] This method is relatively better than the above-mentioned 1, 2, but there are still disadvantages that the reaction temperature is too high and phosgene is easy to escape
At the same time, 1, 2, and 3 all have a common shortcoming: the raw material phosgene is a highly toxic gas, and it does not use industrial operation

Method used

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  • Preparation method of 4-chlorobutyroyl chloride
  • Preparation method of 4-chlorobutyroyl chloride
  • Preparation method of 4-chlorobutyroyl chloride

Examples

Experimental program
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Embodiment 1

[0036] Add 43g (0.5mol) of γ-butyrolactone and 1.5g of zinc chloride to a 250ml three-neck flask, stir and heat up to 100°C, cool down to room temperature, add 150g (0.505mol) of solid phosgene, heat up to 120°C and keep for 18 hours , and recovered under reduced pressure to obtain 53.1g of 4-chlorobutyryl chloride, with a conversion rate of 75.3%.

Embodiment 2

[0038] Add 43g (0.5mol) of γ-butyrolactone, 1.5g of zinc chloride, and 1 drop of DMF into a 250ml three-neck flask, stir and heat up to 100°C, cool down to room temperature, add 75g (0.253mol) of solid phosgene, and heat up to 100°C After 10 hours of heat preservation, 55.62 g of 4-chlorobutyryl chloride was recovered under reduced pressure, with a conversion rate of 78.9%.

Embodiment 3

[0040] Add 43g (0.5mol) of γ-butyrolactone, 1.2g of zinc chloride, and 0.02g of triphenylphosphine oxide into a 250ml three-necked flask, stir and heat up to 100°C, cool down to room temperature, and add 75g (0.253mol) of solid phosgene , raised the temperature to 90° C. for 15 hours, and recovered under reduced pressure to obtain 57.88 g of 4-chlorobutyryl chloride, with a conversion rate of 82.1%.

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Abstract

The invention mainly discloses a preparation method of 4-chlorobutyroyl chloride, which comprises the following steps: selecting solid phosgene and Gamma-butyrolactone as raw materials, wherein the mol ratio of the solid phosgene and the Gamma-butyrolactone is 1.01:(1-0.33):1; putting the Gamma-butyrolactone and lewis acid as a catalyst into a three-neck flask, rising the temperature to 100 DEG C, reducing the temperature to the room temperature, putting the solid phosgene, rising the temperature to 60-140 DEG C, keeping the temperature for 4-40h, reducing the pressure and recovering to obtain the 4-chlorobutyroyl chloride. The invention has simple process, mild reaction condition, high yield, low cost, low toxicity of the used raw materials and no pollution to the environment.

Description

technical field [0001] The invention relates to a preparation method of 4-chlorobutyryl chloride, which can be used to synthesize cyclopropylamine intermediates and other compounds. Background technique [0002] Cyclopropylamine intermediate (formula II) is widely used as one of the main raw materials for the synthesis of fluoroquinolones, and the synthetic method of its key 4-chlorobutyryl chloride (formula I) has multiple reports. [0003] [0004] Synthetic routes suitable for industrial production are mainly divided into two categories according to the different initial ring-opening reagents: one is ring-opening with thionyl chloride, and the other is ring-opening with phosgene. [0005] 1. Use thionyl chloride to open the ring: [0006] "Journal of Fine Chemical Intermediates" VOl.36 No.Jun 2006. Niu Yulan et al. It is introduced that in the synthesis research of 4-chlorobutyryl chloride, thionyl chloride is used as the ring-opening reagent, zinc chloride is used a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C53/50C07C51/58B01J27/138B01J27/125B01J31/26B01J31/02
Inventor 邱家军刘聪侯仲轲潘峰张宜仲田利焕
Owner ZHEJIANG GUOBANG PHARMA
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