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Barraza SJ, Denmark SE. Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions. Synlett. 2017;28(20):2891-2895doi: 10.1055/s-0036-1590882.
Barraza, S. J., & Denmark, S. E. (2017). Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions. Synlett : accounts and rapid communications in synthetic organic chemistry, 28(20), 2891-2895. https://doi.org/10.1055/s-0036-1590882
Barraza, Scott J, and Denmark, Scott E. "Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions." Synlett : accounts and rapid communications in synthetic organic chemistry vol. 28,20 (2017): 2891-2895. doi: https://doi.org/10.1055/s-0036-1590882
Barraza SJ, Denmark SE. Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions. Synlett. 2017 Dec;28(20):2891-2895. doi: 10.1055/s-0036-1590882. Epub 2017 Aug 21. PMID: 29904235; PMCID: PMC5997282.
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Synlett. 2017 Dec;28(20):2891-2895. doi: 10.1055/s-0036-1590882. Epub 2017 Aug 21.

Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions.

Synlett : accounts and rapid communications in synthetic organic chemistry

Scott J Barraza, Scott E Denmark

Affiliations

  1. Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL 61801, USA.

PMID: 29904235 PMCID: PMC5997282 DOI: 10.1055/s-0036-1590882

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.

Keywords: alkylation; bromine; bromoaniline; rearrangement

References

  1. Acc Chem Res. 2003 Apr;36(4):255-63 - PubMed
  2. Angew Chem Int Ed Engl. 2002 May 17;41(10):1699-700 - PubMed

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