Practical chemoselective aromatic substitution: the synthesis of -(4-halo-2-nitrophenyl)benzenesulfonamide through the efficient nitration and halogenation of -phenylbenzenesulfonamide

• Published in: Organic & biomolecular chemistry 2022-07, Vol.2 (27), p.5444-5451
• Main Authors: Yu, Xiao, Zhu, Wenjing, Liu, Hongyan, Liu, Yi, Li, Hongshuang, Han, Junfen, Duan, Guiyun, Bai, Zhushuang, Zhang, Pengfei, Xia, Chengcai
• Format: Article
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d2ob01028c

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(NO 3 ) 2 3H 2 O, Fe(NO 3 ) 3 9H 2 O, and NH 4 NO 3 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. 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.