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Synlett 2013; 24(5): 603-606
DOI: 10.1055/s-0032-1317795
letter
© Georg Thieme Verlag Stuttgart · New York

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

Authors

  • Leonardo S. de Almeida

    Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, Cx. Postal 68545, 21945-970, Rio de Janeiro, Brazil   Fax: +55(21)25627256   eMail: mmattos@iq.ufrj.br   eMail: pesteves@iq.ufrj.br

  • Marcio C. S. de Mattos*

    Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, Cx. Postal 68545, 21945-970, Rio de Janeiro, Brazil   Fax: +55(21)25627256   eMail: mmattos@iq.ufrj.br   eMail: pesteves@iq.ufrj.br

  • 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   Fax: +55(21)25627256   eMail: mmattos@iq.ufrj.br   eMail: pesteves@iq.ufrj.br
Weitere Informationen

Publikationsverlauf

Received: 19. September 2012

Accepted after revision: 23. Januar 2013

Publikationsdatum:
07. Februar 2013 (online)

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Abstract

Moderately deactivated arenes are efficiently brominated by the reaction with tribromoisocyanuric acid (0.34 mol equiv) in trifluoroacetic acid at room temperature in 48–85% isolated yield. This medium avoids the polybromination of the substrate, ­observed in the same reaction performed in 98% H2SO4.

Key words

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

  • References and Notes

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