Dataset Information

Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions.

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.

SUBMITTER: Barraza SJ

PROVIDER: S-EPMC5997282 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions.

Barraza Scott J SJ Denmark Scott E SE

Synlett : accounts and rapid communications in synthetic organic chemistry 20170821 20

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. ...[more]

PMID: 29904235

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Dataset Information

Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions.

Publications

Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions.

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