Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions

Scott J. Barraza, Scott E. Denmark

Research output: Contribution to journalArticlepeer-review


Alkylation of 2-bromoaniline with benzyl bromide under ostensibly basic N-alkylation conditions resulted in migration of bromine from the 2- to the 4-aryl position. Herein we report our studies to elucidate the mechanism of this rearrangement with the objective of suppressing this unexpected outcome. We find that careful choice of reagents is critical, and that this behavior may be extrapolated to alkylation reactions of electron-rich bromo- and iodoanilines in general.

Original languageEnglish (US)
Pages (from-to)2891-2895
Number of pages5
Issue number20
StatePublished - Dec 18 2017


  • alkylation
  • bromine
  • bromoaniline
  • rearrangement

ASJC Scopus subject areas

  • Organic Chemistry


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