Tribromoisocyanuric Acid in Trifluoroacetic Acid: An Efficient System for Smooth Brominating of Moderately Deactivated Arenes

Leonardo S. de Almeida, Marcio C. S. de Mattos*, Pierre M. Esteves*

*Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, Cx. Postal 68545, 21945-970, Rio de Janeiro, Brazil, Email: mmattosiq.ufrj.br, pestevesiq.ufrj.br

L. S. de Almeida, M. C. S. de Mattos, P. M. Esteves, Synlett, 2013, 24, 603-606.

DOI: 10.1055/s-0032-1317795

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Abstract

Moderately deactivated arenes are efficiently brominated with 0.34 eq. tribromoisocyanuric acid in trifluoroacetic acid at room temperature. The use of trifluoroacetic acid avoids the polybromination of the substrate, as can be observed in the same reaction performed in 98% H₂SO₄.

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Key Words

arenes, electrophilic halogenation, bromination, deactivated aromatic compounds, tribromoisocyanuric acid

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ID: J60-Y2013-0690