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.
引用
收藏
页码：2321 / 2323
页数：3
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