Ammonium Chloride → 4-[(4-tert-Butylphenyl)sulfanyl]-3-chloroaniline

Participants

Reaction Conditions

Reaction Steps

1-(4-tert-butyl-phenylsulfanyl)-2-chloro-4-nitro-benzene was dissolved in acetone (15 mL), then saturated aqueous NH4Cl (5 mL) was added and the mixture was cooled to 0° C. Solid zinc powder (3.7 g, 56 mmol) was added in portions over 10 min with rapid stirring. The mixture was allowed to warm to rt and was stirred 3 h. The mixture was diluted with EtOAc (250 mL), dried, and filtered through Celite®. Removal of solvent gave a yellow residue, which was used without further purification. MS (ESI): mass calcd. for C16H18ClNS, 291.1; m/z found 292.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 7.33-7.21 (m, 3H), 6.95 (d, J=8.5, 2H), 6.77 (d, J=2.4, 1H), 6.55 (dd, J=8.4, 2.4, 1H), 5.80 (s, 2H), 1.22 (s, 9H).

Provenance & Evidence