2-Bromonaphthalene → HCID 22493510, compound

Participants

Reaction Conditions

Reaction Steps

Butyllithium (31 ml, 72 mmol) was added to a mixture of 2-bromonaphthalene (14.9 g, 72.1 mmol) and diethyl ether (300 ml) at −70° C. The resulting mixture was stirred at −70° C. for 30 minutes. A mixture of 3-quinuclidinone and diethyl ether (150 ml) was added at −70° C. The mixture was stirred at −70° C. for 1 hour and was then allowed to reach room temperature. Aqueous sodium hydroxide (400 ml, 1 M) was added. The phases were separated and the aqueous phase was extracted with diethyl ether (100 ml). The combined organic phases were purified by chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. Yield 2.03 g (11%).

Provenance & Evidence