Regioselective one-pot bromination of aromatic amines
Resource type
Authors/contributors
- Smith, M.B. (Author)
- Guo, L. (Author)
- Okeyo, S. (Author)
- Stenzel, J. (Author)
- Yanella, J. (Author)
- LaChapelle, E. (Author)
Title
Regioselective one-pot bromination of aromatic amines
Abstract
(Matrix Presented) 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-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.
Publication
Organic Letters
Date
2002
Volume
4
Issue
14
Pages
2321-2323
Journal Abbr
Org. Lett.
Citation Key
smithRegioselectiveOnepotBromination2002
ISSN
15237060 (ISSN)
Archive
Scopus
Language
English
Extra
37 citations (Crossref) [2023-10-31]
Citation
Smith, M. B., Guo, L., Okeyo, S., Stenzel, J., Yanella, J., & LaChapelle, E. (2002). Regioselective one-pot bromination of aromatic amines. Organic Letters, 4(14), 2321–2323. Scopus. https://doi.org/10.1021/ol0259600
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