Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions

Scott J. Barraza, Scott E. Denmark

Research output: Contribution to journalArticle

Abstract

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
JournalSynlett
Volume28
Issue number20
DOIs
StatePublished - Dec 18 2017

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Alkylation
Bromine
Electrons
3-bromoaniline

Keywords

  • alkylation
  • bromine
  • bromoaniline
  • rearrangement

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions. / Barraza, Scott J.; Denmark, Scott E.

In: Synlett, Vol. 28, No. 20, 18.12.2017, p. 2891-2895.

Research output: Contribution to journalArticle

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