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Preparation method of 1-chloro-4-phenyl butane

A technology of phenylbutane and dichlorobutane, applied in the field of preparation of pharmaceutical intermediates, can solve the problem of high cost and achieve the effects of low cost, convenient operation and mild reaction conditions

Inactive Publication Date: 2014-01-29
KUNSHAN RIKITA PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In order to overcome above-mentioned defect, the present invention provides a kind of preparation method of the 1-chloro-4-phenylbutane that overcomes the problem of high cost in the preparation method of existing 1-chloro-4-phenylbutane

Method used

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  • Preparation method of 1-chloro-4-phenyl butane
  • Preparation method of 1-chloro-4-phenyl butane

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Put 1,4-dichlorobutane (1000g, 7.87mol, 6.0eqv.) into a 2000ml four-necked flask, and add anhydrous aluminum chloride (8.7g, 0.065mol, 0.05eqv.) under nitrogen protection , Mechanical stirring, ice water cooling, at 3 oC Begin to add benzene (102.5g, 1.31mol) dropwise, add it in 5 hours, then continue to stir for 10 minutes, add 150g of pure water dropwise in 8 minutes, stir for 30 minutes and then stand at room temperature, separate the upper layer (water layer, containing chlorine Aluminium), washed three times to pH 6~7, the organic layer is rectified under normal pressure (tower height is 100cm), and a small amount of benzene (21g) is recovered. It can be used after drying through molecular sieve, containing 1~2% 1,4-dichlorobutane Alkane does not affect the application, bp. 77~80 oC ), and then collect the second fraction 1,4-dichlorobutane (828 grams, bp. 152~154 oC , Can be applied after being dried by molecular sieve), and then the collected fraction is tetrali...

Embodiment 2

[0027] 17.3g (0.13mol, 0.10eqv.) of anhydrous aluminum chloride, other operations are the same as in Example 1, and the yield is 69%.

Embodiment 3

[0029] 1,4-Dichlorobutane 500g (3.94mol, 3.0eqv.), other operations are the same as in Example 1, the yield is 64%.

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Abstract

The invention discloses a preparation method of 1-chloro-4-phenyl butane. The preparation method comprises the following steps: adding a catalyst aluminum chloride into dry excessive 1,4-dichlorobutane; slowly dropwise adding dry benzene for reaction while stirring; and performing aftertreatment to recycle the non-completely reacted raw materials, and performing reduced-pressure distillation to obtain the product. The preparation method disclosed by the invention can be finished only by a one-step reaction, and does not need Grignard reaction and phenyl butanol; the cost is low, and the reaction conditions are mild; the preparation method is convenient to operate and suitable for industrialization.

Description

Technical field [0001] The invention relates to a preparation method of pharmaceutical intermediates, in particular to a preparation method of 1-chloro-4-phenylbutane. Background technique [0002] 1-Chloro-4-phenylbutane (1-Chloro-4-phenylbutane), the molecular formula is C 10 H 13 Cl, molecular weight is 168.66, CAS number is 4830-93-7, structural formula is: [0003] [0004] It is a colorless liquid, and it is an important intermediate of the new anti-asthma drug Pranlukast. There are two main methods for its synthesis: [0005] A. Formal reaction method, using phenylmagnesium chloride or benzylmagnesium chloride to react with 1,4-bromochlorobutane or 1,3-bromochloropropane respectively. Although the yield of this method is higher than 85%, the cost is higher. It is difficult to apply the solvent tetrahydrofuran (containing water) after recovery. For details, please refer to related documents: 1. EP1369405 (2003); 2. Martin, Ruben; Fuerstner, Alois; Angewandte Chemie, Inter...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C22/04C07C17/266
Inventor 陈发普高朋何大宇吴俊飞
Owner KUNSHAN RIKITA PHARMA
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