精细化工中间体2024,Vol.54Issue(2) :59-62.DOI:10.19342/j.cnki.issn.1009-9212.2024.02.014

乙基苯炔基四氟联苯胺的合成研究

Synthesis of 4'-(4-Ethyl-phenylethynyl)-3,5,2',6'-tetrafluoro-biphenyl-4-ylamine

郭晶晶 王冠 马良秀 叶海伟
精细化工中间体2024,Vol.54Issue(2) :59-62.DOI:10.19342/j.cnki.issn.1009-9212.2024.02.014

乙基苯炔基四氟联苯胺的合成研究

Synthesis of 4'-(4-Ethyl-phenylethynyl)-3,5,2',6'-tetrafluoro-biphenyl-4-ylamine

郭晶晶 1王冠 1马良秀 2叶海伟1
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作者信息

  • 1. 台州职业技术学院化学制药研究所,浙江 台州 318000
  • 2. 天台宜生生化科技有限公司,浙江天台 317200
  • 折叠

摘要

乙基苯炔基四氟联苯胺(3)是炔烃类液晶关键中间体,针对氟苯乙炔苯硼酸稳定性差,3合成难问题,通过构建二氟碘苯胺与联硼酸频那醇酯反应中间体二氧硼烷二氟苯胺(2),与对乙基苯乙炔、二氟溴碘苯Sonogashira偶联产物2-溴-1,3-二氟-5-(4-乙基苯乙炔基)苯(1)的Suzuki偶联,合成目标产物3.其结构经1HNMR、ESI-MS等确证,并对合成工艺进行了优化,总收率达70%,纯度99.5%(HPLC).

Abstract

4'-(4-Ethyl-phenylethynyl)-3,5,2',6'-tetrafluoro-biphenyl-4-ylamine(3)is a key intermediate of fluorotolane liquid crystal compounds.Due to the poor stability of 2,6-difluoro-4-phenylethynyl-phenylboronic acid,it is difficult for the synthesis of 3.However,the target product 3 can be synthesized via Suzuki Coupling with 2,which is the intermediate of 2,6-difluoro-4-iodoaniline and bis(pinacolato)diboron,and 1,which is the sonogashira coupling product of 4-ethylphenylacetylene and 2-bromo-1,3-difluoro-5-(4-ethylphenylethynyl)benzene.The structure was confirmed by 1H NMR,ESI-MS,etc.,and the synthetic process was optimized with an overall yield of 70%,and the purity was 99.5%(HPLC).

关键词

乙基苯炔基四氟联苯胺/二氧硼烷二氟苯胺/工艺优化

Key words

4'-(4-ethyl-phenylethynyl)-3,5,2',6'-tetrafluoro-biphenyl-4-ylamine/2,6-difluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine/process optimization

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基金项目

台州市科技计划(21gyb29)

台州市科技计划(22ywa61)

出版年

2024
精细化工中间体
湖南化工研究院

精细化工中间体

CSTPCD
影响因子:0.236
ISSN:1009-9212
参考文献量1
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