Dimethyl Sulfoxide → 2-(3-Bromo-1H-pyrrol-1-yl)pyridine

Participants

Reaction Steps

Bromotrimethylsilane (10.9 mL, 84 mmol) was added to DMSO (5.7 mL, 84 mmol) in MeCN (200 mL) at 0° C. After stirring for 10 min, 2-(1H-pyrrol-1-yl)pyridine (10 g, 70 mmol) in MeCN (50 mL) was added. The reaction mixture was stirred at 0° C. and allowed to reach rt over 3 h. H2O (150 mL) and EtOAc (150 mL) were added and the reaction mixture was shaken, the EtOAc layer was separated and the aqueous layer shaken with EtOAc (3×150 mL). The combine organic layers were dried over Na2SO4 and concentrated to a brown oil. LCMS indicated good conversion to 2-(3-bromo-1H-pyrrol-1-yl)pyridine and this was used without further purification. (MS (ESI) 224 (M+H)+.

Provenance & Evidence