Regioselective one-pot bromination of aromatic amines.
[reaction: see text] Treatment of aniline with n-butyllithium and then trimethyltin chloride gave the tin amide (PhNH-SnMe(3)) 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-bromoaniline. 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.
Smith
Michael B
MB
Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, Connecticut 06269-3060, USA. smith@nucleus.chem.uconn.edu
Guo
Lisa  Chen
L
Okeyo
Sherrad
S
Stenzel
Jason
J
Yanella
James
J
LaChapelle
Eric
E