Xiao Yu, Wenjing Zhu, Hongyan Liu
Jun 30, 2022
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Journal
Organic & biomolecular chemistry
Abstract
A novel route involving the metal-promoted tandem nitration and halogenation of N-phenylbenzenesulfonamide to synthesize N-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed. The method shows highly practical chemoselective and functional group compatibility. In addition, it employs insensitive and inexpensive Cu(NO3)2·3H2O, Fe(NO3)3·9H2O, and NH4NO3 as the nitration reagents, and it provides a direct approach for the preparation of 4-halo-2-nitroaniline, which is a crucial intermediate for the synthesis of benzimidazoles and quinoxaline derivatives.