Bromine → 5-Bromo-3-(phenylthio)pyridin-2-amine

Participants

Reaction Steps

A 500 mL flask was charged with 2-nitro-3-(phenylthio)pyridine (16.3 g, 70.2 mmol) and AcOH (250 mL) and cooled in a water bath. Zinc (22.9 g, 351 mmol) was slowly added and stirred for 5 minutes. The reaction was filtered through celite and the cake washed with CH2Cl2. The CH2Cl2 was removed in vacuo and solution reacted with slow addition of bromine (3.6 mL, 70.2 mmol). After 10 minutes, the HOAc was removed in vacuo and partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel (1.5 L SiO2 and 30% EtOAc in hexanes) to afford the title compound (18.2 g, 92.21% yield)

Provenance & Evidence