Bromine → 3-BROMO-8a-BUTYL-6-HYDROXY-8,8a-DIHYDROCYCLOPENTA[a]INDEN-2(1H)-ONE

Participants

Reaction Conditions

Reaction Steps

Bromine (0.005 mL, 0.095 mmol) was added to an ice-cold mixture of 8a-butyl-6-hydroxy-8,8a-dihydrocyclopenta[a]inden-2(1H)-one (23 mg, 0.095 mmol) and NaHCO3 (40 mg, 0.48 mmol) in CCl4 (0.3 mL). The resulting mixture was stirred at 0-5° C. for 45 minutes, then diluted with CH2Cl2 (30 mL) and washed with water (30 mL). The aqueous phase was back-extracted with CH2Cl2 (2×10 mL). The combined organics were washed with saturated aqueous Na2S2O3, dried over MgSO4, filtered, and evaporated under vacuum to provide an off-white solid. Recrystallization from hexane/CH2Cl2 afforded 3-bromo-8a-butyl-6-hydroxy-8,8a-dihydrocyclopenta[a]inden-2(1H)-one as small, white needles.

Provenance & Evidence