2-Chloro-1-(methylsulfanyl)-4-nitrobenzene → 3-Chloro-4-(methylthio)aniline

Participants

Reaction Steps

To a mixture of the compound from stage (i) (14.08 g, 69 mmol) in acetic acid (300 mL) and water (60 mL) was added Fe powder (23 g, 412 mmol) and the reaction mixture was swirled until all the starting material had dissolved. The mixture was left to stand for 1.5 h and the acetic acid was then removed under reduced pressure. The residue was taken up in sat NaHCO3 (aq) (500 mL) and EtOAc (500 mL) and filtered through Arbacel®. The layers were separated, the aqueous phase was extracted with EtOAc (300 mL) and the combined organics were washed with brine, dried (MgSO4) and the solvent was removed in vacuo to give the title compound (11.52 g, 96%) as a beige solid; δH (400 MHz, CDCl3) 2.38 (3H, s), 3.66 (2H, br), 6.53 (1H, dd), 6.70 (1H, d), 7.12 (1H, d); MS m/z (ES+) 174 (MH+).

Provenance & Evidence