Synthetic Communications

Reexamination of the Bromination of 2-Nitrobenzaldehyde with NBS or NaBr-NaIO4 in Sulfuric Acid

MM Cummings, BCG Söderberg

Index: Cummings, Matthew M.; Soederberg, Bjoern C. G. Synthetic Communications, 2014 , vol. 44, # 7 p. 954 - 958

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Citation Number: 2

Abstract

Two literature procedures for selective bromination of 2-nitrobenzaldehyde using N-bromosuccinimide (NBS) or NaBr-NaIO 4 in sulfuric acid were examined. In contrast to the reports that 4-bromo-2-nitrobenzaldehyde is formed as a single product in good yield, reactions using NBS gave a number of isomeric mono- and dibrominated products identified by spectroscopical methods and by sodium borohydride reduction to the corresponding benzyl alcohol, and reactions ...