Efficient and Practical Synthesis of 3′,4′,5′-Trifluoro-[1,1′-biphenyl]-2-amine: A Key Intermediate of Fluxapyroxad

被引：13

作者：

Li, Zhenhua ^{[1
,2
]}

Zhang, Xuchao ^{[1
]}

Qin, Jinjing ^{[1
]}

Tan, Zhiyong ^{[1
]}

Han, Meizhen ^{[2
]}

Jin, Guoqiang ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Minist Educ, Key Lab Green Pharmaceut Technol & Related Equipm, Chao Wang Rd 18th, Hangzhou 310014, Zhejiang, Peoples R China

[2] Zhejiang Univ Technol, Natl Engn Res Ctr Proc Dev Act Pharmaceut Ingredi, Collaborat Innovat Ctr Yangtze River Delta Reg, Green Pharmaceut, Hangzhou 310014, Zhejiang, Peoples R China

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2019年 / 23卷 / 09期

基金：

中国国家自然科学基金;

关键词：

3',4',S'-trifluoro-1-[1,1'-biphenyt]-2-amine; Suzuki-Miyaura coupling; biphenyl; Fluxapyroxad; o-chloronitrobenzene; CROSS-COUPLING REACTIONS; SDHI FUNGICIDE RESISTANCE; ARYL CHLORIDES; CHEMOSELECTIVE REDUCTION; PALLADIUM CATALYSTS; NITROARENES; ANILINES; WATER; ALKENYLATION; DISCOVERY;

D O I：

10.1021/acs.oprd.9b00208

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An improved and practical method is reported here for accessing 3',4',5'-trifluoro-[1,1'-biphenyl]-2-amine (1), a key intermediate for Fluxapyroxad. The overall yield for the preparation of 1 was 73%, with a purity of 99.88%, after a three-step process. More importantly, this process was an improvement in the manufacture of biphenyl compounds by Suzuki-Miyaura coupling, which enabled catalyst loading as low as 0.04 mol %. This method could provide an economic and environment friendly process leading to extensive prospects in industrial applications.

引用

页码：1881 / 1886

页数：6

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