Bromine → 5-Bromo-2,3-dihydro-1-benzothiophene

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Reaction Steps

Iron powder (10.4 mg, 1.47 mmol) was added to a solution of 2,3-dihydrobenzo[b]thiophene 112 (400 mg, 2.94 mmol) in dichloromethane (5.9 mL). Bromine (0.15 mL, 2.94 mmol) was added dropwise to the mixture with stirring under ice-cooling. This mixture was stirred at the same temperature for 30 minutes. Saturated aqueous sodium hydrogen carbonate solution was added to the mixture and this was extracted with dichloromethane. The organic layer was washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide the desired product 113 (396 mg, 63%).

Provenance & Evidence