Potassium Hydroxide → 2-(2-Methoxy-phenylsulfanyl)-5-nitro-benzoic Acid

Participants

Reaction Steps

2-Methoxythiophenol (9.9 ml, 81.29 mmol) was added to a solution of KOH (18.24 g, 325.18 mmol) in water (80 ml) degassed for 15 minutes. 2-Bromo-5-nitrobenzoic acid (20.0 g, 81.29 mmol) and copper bronze (258 mg, 4.06 mmol) were added to the reaction mixture, which was refluxed overnight. The reaction was stopped and the mixture was filtered through a celite pad and washed with 2M NaOH then water (50 ml). The filtrate was acidified (pH 1) with concentrated HCl. The precipitate formed was filtered and dried overnight in a vacuum oven (50° C.) to give the crude title compound (26.0 g) as a pale yellow solid. The product was used without further purification.

Provenance & Evidence