Bromine → 5-Bromo-4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine

Participants

Reaction Steps

To a solution of 4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine (463 mg, 2.40 mmol) in dichloromethane (10 mL) were added sodium hydrogen carbonate (504 mg, 6.00 mmol) and bromine (959 mg, 6.00 mmol) at room temperature, and the mixture was stirred for 9 hr. An aqueous sodium thiosulfate solution was added to the reaction solution, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→30/70) to give the title compound (522 mg, yield 80%).

Provenance & Evidence