世界农药2024,Vol.46Issue(5) :54-60.DOI:10.16201/j.cnki.cn10-1660/tq.2024.05.11

基于微通道技术合成2-氨基-5-氟-3',4'-二氯联苯

Synthesis of 2-amino-5-fluoro-3',4'-dichlorobiphenyl based on microchannel technology

严泽华 何星帅 吴浩 尹凯
世界农药2024,Vol.46Issue(5) :54-60.DOI:10.16201/j.cnki.cn10-1660/tq.2024.05.11

基于微通道技术合成2-氨基-5-氟-3',4'-二氯联苯

Synthesis of 2-amino-5-fluoro-3',4'-dichlorobiphenyl based on microchannel technology

严泽华 1何星帅 1吴浩 1尹凯2
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作者信息

  • 1. 浙江吉泰新材料股份有限公司,浙江 绍兴 312369
  • 2. 浙江吉泰新材料股份有限公司,浙江 绍兴 312369;浙江南郊化学有限公司,浙江 绍兴 312369
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摘要

2-氨基-5-氟-3',4'-二氯联苯是琥珀酸脱氢酶抑制剂(SDHI)类杀菌剂—联苯吡菌胺的重要中间体.基于微通道技术,以 3,4-二氯苯胺为原料,经重氮化、中和、与对氟苯胺偶联得到 2-氨基-5-氟-3',4'-二氯联苯.系统考察了影响重氮化、中和、偶联 3步对反应的影响,并得出优化条件:盐酸与3,4-二氯苯胺当量6:1,亚硝酸钠与3,4-二氯苯胺当量 1.1︰1,成盐反应温度60℃,重氮反应温度 25℃,氢氧化钠当量6.5︰1,中和温度 25℃,偶联最佳温度 120℃,对氟苯胺当量 10︰1.在此优化条件下合成 2-氨基-5-氟-3',4'-二氯联苯粗品含量 85%,精制后含量可以达到 98.5%,2 步总收率65%.

Abstract

2-Amino-5-fluoro-3',4'-dichlorobenzene is an important intermediate of succinate dehydrogenase inhibitor(SDHI)fungicide,bixafen.Based on microchannel technology,3,4-dichloroaniline was used as raw material to obtain 2-amino-5-fluoro-3',4'-dichlorobiphenyl through diazotization,neutralization,and coupling with p-fluoroaniline.The system investigated the effects of the three steps of diazotization,neutralization,and coupling on the reaction,and obtained optimized conditions:hydrochloric acid and 3,4-dichloroaniline equivalent 6︰1,sodium nitrite and 3,4-dichloroaniline equivalent 1.1︰1,salt formation reaction temperature 60℃,diazotization reaction temperature 25℃,sodium hydroxide equivalent 6.5︰1,neutralization temperature 25℃,optimal coupling temperature 120℃,and p-fluoroaniline equivalent 10︰1.Under these optimized conditions,2-amino-5-fluoro-3',4'-dichlorobiphenyl was synthesized with a crude content of 85% .After refinement,the content can reach 98.5%,and the total yield of the two steps is 65% .

关键词

2-氨基-5-氟-3',4'-二氯联苯/联苯吡菌胺/微通道技术

Key words

2-amino-5-fluoro-3',4'-dichlorobiphenyl/bixafen/microchannel technology

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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3
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