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Process for producing 4'-bromomethyl-2-cyanobiphenyl

一种氰基联苯、溴甲基的技术，应用在制备4’-溴甲基-2-氰基联苯领域，能够解决容积效率降低、不是、水含量增加等问题，达到提高容积效率的效果

Inactive Publication Date: 2006-11-22
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since this method requires the use of 48% aqueous hydrobromic acid and 50% aqueous hydrogen peroxide, the water content increases and the volumetric efficiency decreases in this system
In addition, because of the high concentration of hydrogen peroxide aqueous solution that needs to be used, its handling is dangerous, and this method is not an industrially advantageous method

Method used

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  • Process for producing 4'-bromomethyl-2-cyanobiphenyl

Examples

Experimental program
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Effect test

Embodiment 1

[0032] 4'-Methyl-2-cyanobiphenyl (105 g, 0.54 mole) and sodium bromate (12.3 g, 0.082 mole) were added to monochlorobenzene (300 g), and the internal temperature was set to 65°C. After adding 2,2'-azobis(2-methylbutyronitrile) (2.0 g, 0.010 mol), bromine (45.6 g, 0.29 mol) was added dropwise over 5 hours, and the mixture was heated for 1 hour. Then, the obtained inorganic salt was filtered off, and the reaction temperature was cooled to 5°C. Precipitated crystals were collected by filtration to obtain 4'-bromomethyl-2-cyanobiphenyl (110 g, 0.405 mol) (yield 75%).

Embodiment 2

[0034] Substitute 2,2'-azobis(2-methylbutyronitrile) with 2,2'-azobis(2,4-dimethylvarelonitrile) (2.5 g, 0.010 mol) Similar reaction and treatment in Example 1 gave 4'-bromomethyl-2-cyanobiphenyl (113 g, 0.416 mol) (yield 77%).

Embodiment 3

[0036]By adding water (0.3g) in monochlorobenzene (300g), carry out similar reaction and treatment as in Example 1, obtain 4'-bromomethyl-2-cyanobiphenyl (114g, 0.421mol) ( Yield 78%).

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Abstract

The present invention relates to a method of producing 4'-bromomethyl-2-cyanobiphenyl, which includes reacting 4'-methyl-2-cyanobiphenyl with bromine in the presence of a radical initiator and an oxidant. According to the present invention, 4'-bromomethyl-2-cyanobiphenyl useful as a starting material of a pharmaceutical product can be produced industrially advantageously because, using an oxidant, bromine can be reproduced from hydrogen bromide by-produced as the bromination reaction proceeds, which in turn enables prevention of inhibition of the reaction due to hydrogen bromide, coloration due to bromine and the like.

Description

technical field [0001] The invention relates to a method for conveniently preparing 4'-bromomethyl-2-cyanobiphenyl in industry, and 4'-bromomethyl-2-cyanobiphenyl can be used as a synthetic intermediate of pharmaceutical products. Background technique [0002] As disclosed in JP-A-63-23868, 4'-bromomethyl-2-cyanobiphenyl is a synthetic intermediate useful as a pharmaceutical product such as a compound having angiotensin II antagonism. There are various methods for the preparation of 4'-bromomethyl-2-cyanobiphenyl, which have been previously disclosed. [0003] JP-A-6-192170 describes the bromination of 4-methylbiphenyl compounds using a brominating agent such as N-bromosuccinimide in a halogenated hydrocarbon solvent in the presence of an azobis compound Methods. However, this method uses expensive N-bromosuccinimide or the like as a bromination agent, and is industrially disadvantageous. [0004] JP-A-8-127562 describes a process for producing 4'-bromomethyl-2-cyanobiphe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/30C07C255/50
CPCC07C253/30C07C255/50
Inventor 山田诚二石原显仲松敏夫
Owner SUMITOMO CHEM CO LTD