世界农药2024,Vol.46Issue(1) :38-41,49.DOI:10.16201/j.cnki.cn10-1660/tq.2024.01.06

联苯吡菌胺关键中间体3',4'-二氯-5-氟-1,1'-联苯-2-胺的合成

Synthesis of the key itermediate 3',4'-dichloro-5-fluoro-1,1'-biphenyl-2-amine of bixafen

黄晓瑛 尚宇 王威 王列平 毛明珍
世界农药2024,Vol.46Issue(1) :38-41,49.DOI:10.16201/j.cnki.cn10-1660/tq.2024.01.06

联苯吡菌胺关键中间体3',4'-二氯-5-氟-1,1'-联苯-2-胺的合成

Synthesis of the key itermediate 3',4'-dichloro-5-fluoro-1,1'-biphenyl-2-amine of bixafen

黄晓瑛 1尚宇 2王威 1王列平 1毛明珍1
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作者信息

  • 1. 西安近代化学研究所 氟氮化工资源高效开发与利用国家重点实验室,西安 710065
  • 2. 陕西省环境监测中心站,西安 710054
  • 折叠

摘要

为获得联苯吡菌胺关键中间体 3',4'-二氯-5-氟-1,1'-联苯-2-胺的适合工业化生产工艺路线,对其合成工艺进行了优化.以3,4-二氯溴苯和2-溴-4-氟苯胺为原料,经格氏和Suzuki偶联2步反应合成了3',4'-二氯-5-氟-1,1'-联苯-2-胺,其结构经 1H NMR、MS表征确证,并对合成条件进行了优化.优化条件下,3',4'-二氯-5-氟-1,1'-联苯-2-胺合成总收率 61.9%,纯度 98%.该工艺成本低,收率高,具有工业化生产前景.

Abstract

To obtain a new suitable industrial route of 3',4'-dichloro-5-fluoro-1,1'-biphenyl-2-amine,which was the key intermediate of bixafen,the synthesis process was optimized.3',4'-Dichloro-5-fluoro-1,1'-biphenyl-2-amine was synthesized using 3,4-dichlorobromobenzene and 2-bromo-4-fluoroaniline as starting material by two steps of grignard and Suzuki coupling reaction.The structure was confirmed by 1H NMR,MS,and the synthesis conditions were optimized.Under the optimal reaction conditions,the total yield of 4'-chloro-2-aminobiphenyl was over 61.9%based on 3,4-dichlorobromobenzene,the purity was 98%.This process has the feature of low cost,high yield and has the prospect of industrial scale manufacture.

关键词

3',4'-二氯-5-氟-1,1'-联苯-2-胺/合成/联苯吡菌胺

Key words

3',4'-dichloro-5-fluoro-1,1'-biphenyl-2-amine/synthesis/bixafen

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基金项目

陕西省科技厅重点研发计划项目(2022GY-202)

国防科技重点实验室基金(2022-JCJQ-LB-037)

出版年

2024
世界农药
上海市农药研究所

世界农药

影响因子:0.494
ISSN:1009-6485
参考文献量4
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