56990-05-7Relevant articles and documents
Reexamination of the bromination of 2-nitrobenzaldehyde with NBS or NaBr-NaIO4 in sulfuric acid
Cummings, Matthew M.,Soederberg, Bjoern C. G.
supporting information, p. 954 - 958 (2014/03/21)
Two literature procedures for selective bromination of 2-nitrobenzaldehyde using N-bromosuccinimide (NBS) or NaBr-NaIO4 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 using NaBr-NaIO4 did not furnish any product. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]