title: Regioselective one-pot bromination of aromatic amines.
abstract: [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.
authors.affiliation: Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, Connecticut 06269-3060, USA. smith@nucleus.chem.uconn.edu
authors.forename: Michael B
authors.initials: MB
authors.lastname: Smith
authors.forename: Lisa  Chen
authors.initials: L
authors.lastname: Guo
authors.forename: Sherrad
authors.initials: S
authors.lastname: Okeyo
authors.forename: Jason
authors.initials: J
authors.lastname: Stenzel
authors.forename: James
authors.initials: J
authors.lastname: Yanella
authors.forename: Eric
authors.initials: E
authors.lastname: LaChapelle