Sodium Hydroxide → 3,5-Dibromobenzene-1-thiol

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (1.96 g, 49 mmol) was added to a solution of S-(3,5-dibromophenyl) diethylthiocarbamate (12 g, 32.7 mmol) (Preparation 47) in methanol (33 ml) and the mixture was heated at reflux for 15 hours. The mixture was cooled to 20° C. and concentrated under reduced pressure. The residue was partitioned between dichloromethane (90 ml) and water (250 ml) and the aqueous layer was further extracted with dichloromethane (90 ml). The combined organic layers were washed with a solution of sodium hydroxide (1N, 100 ml). The combined aqueous layers were cooled to 0° C. and the pH was adjusted to 2 by the addition of concentrated hydrochloric acid, giving a white suspension. This suspension was extracted with dichloromethane (2×250 ml) and the combined extracts were washed with brine (25 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave the title compound as a yellow solid (6.7 g).

Provenance & Evidence