Imidazole → 2-(2-Bromoethyl)naphthalene

Participants

Reaction Steps

A solution of triphenylphosphine (0.57 g, 2.2 mmol) and N-bromosuccinimide (0.39 g, 2.2 mmol) in anhydrous dichloromethane (4 mL) was stirred for 10 minutes. 2-Naphthalenethanol (0.25 g, 1.45 mmol) was added, followed inmmediately by imidazole (0.25 g, 1.45 mmol) and the mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between H2O and dichloromethane. The aqueous layer was extracted with diethyl ether (2×20 mL) and the combined organic extracts were dried over MgSO4 and evaporated to dryness. The crude residue was purified by column chromatography through a plug of silica gel eluting with 10% ethyl acetate in hexanes to afford a colorless solid 214 (0.29 g, 86%).

Provenance & Evidence