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Synthesis 2009(8): 1305-1308  
DOI: 10.1055/s-0028-1088016
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Electrophilic Bromination of meta-Substituted Anilines with N-Bromosuccin­imide: Regioselectivity and Solvent Effect

Sandra Bartoli, Amalia Cipollone, Antonella Squarcia, Andrea Madami, Daniela Fattori*
Menarini Ricerche S.p.A., via Tito Speri 10, 00040 Pomezia (Rm), Italy
Fax: +39(06)91184462; e-Mail: dfattori@menarini-ricerche.it;
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Publication History

Received 5 November 2008
Publication Date:
16 March 2009 (online)

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Abstract

N-Bromosuccinimide-mediated electrophilic aromatic bromination of a series of anilines substituted with an electron-withdrawing group in the meta position was investigated. The regioselectivity of the reaction is markedly dependent on the polarity of the solvent and the bromination reaction can be tuned by appropriate selection of the reaction medium.

Key words

bromine - electrophilic aromatic substitution - regioselectivity - solvent effects

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