Regioselective one-pot bromination of aromatic amines

被引：41

作者：

Smith, MB

Guo, L

Okeyo, S

Stenzel, J

Yanella, J

LaChapelle, E

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

[2] So Connecticut State Univ, New Haven, CT 06515 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 14期

关键词：

D O I：

10.1021/ol0259600

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Treatment of aniline with n-butyllithium and then trimethyltin chloride gave the tin amide (PhNH-SnMe3) in situ. Without isolation of the tin amide, reaction with bromine and workup with aqueous fluoride ion gave p-bromoaniline in 76% yield, with no dibromoaniline or o-bromoanillne. Application of this sequence to 11 different aromatic amines gave selective bromination in 36-91% yields, without formation of dibromides. This constitutes a good general method for the regioselective bromination of aromatic amines.

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页码：2321 / 2323

页数：3

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