A Convenient Synthesis of 2,2-Dibromo-1-arylethanones by Bromination of 1-Arylethanones with the H₂O₂-HBr System

Alexander O. Terent'ev*, Sergey V. Khodykin, Igor B. Krylov, Yuri N. Ogibin, Gennady I. Nikishin

*N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia, Email: terentevioc.ac.ru

A. O. Terent'ev, S. V. Khodykin, I. B. Krylov, Y. N. Ogibin, G. I. Nikishin, Synthesis, 2006, 1087-1092.

DOI: 10.1055/s-2006-926386

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Abstract

1-Arylethanones and related compounds are rapidly brominated in dioxane with the H₂O₂-HBr aq system, resulting in the replacement of two hydrogen atoms in the methyl group with bromine. The reaction is also accompanied by bromination of the aromatic ring provided that the latter contains electron-donating substituents.

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Key Words

acetophenones, 1-arylethanones, 2,2-dibromo-1-aryl­ethanones, bromination, hydrogen peroxide

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ID: J66-Y2006-970