PDF herunterladen
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;
Weitere Informationen

Publikationsverlauf

Received 5 November 2008
Publikationsdatum:
16. März 2009 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

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

    References

  • 1 Couper AS. Ann. Chim. Phys.  1858,  53:  469 
    Google Scholar
  • 2a Lenoir D. Angew. Chem. Int. Ed.  2003,  42:  854 
    Google Scholar
  • 2b Vasilyev AV. Lindemann SV. Kochi JK. New J. Chem.  2002,  26:  582 
    Google Scholar
  • 3 Carey FA. Sundberg RJ. In Advanced Organic Chemistry. Part A: Structure and Mechanism   Plenum Press; New York: 1984.  p.489-503  
    Google Scholar
  • 4 Mitchell RH. Lai Y.-H. Williams RV. J. Org. Chem.  1979,  44:  4733 
    CrossrefGoogle Scholar
  • 5 De Almeida LS. Esteves PM. de Mattos MCS. Synthesis  2006,  221 
    Artikel in Thieme ConnectGoogle Scholar
  • 6 Prakash GKS. Mathew T. Hoole D. Esteves PM. Wang Q. Rasul G. Olah GA. J. Am. Chem. Soc.  2004,  126:  15700 
    Google Scholar
  • 7 Ganguly NC. De P. Dutta S. Synthesis  2005,  1101 
    Google Scholar
  • 8 Hammond GS. Hawthorne MF. In Steric Effects in Organic Chemistry   Wiley; New York: 1956.  p.164-200  
    Google Scholar