Water → HCID 22731331, compound

Participants

Reaction Steps

A stirred, cooled (ice-bath) suspension of aluminum chloride (0.25 g, 1.7 mmol) in 3 mL of anhydrous dichloromethane was treated with acetyl chloride (0.2 mL, 2.6 mmol) under argon. A solution of 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (Intermediate 2, 0.22 g) in 1.5 mL of anhydrous dichloromethane was cannulated into the clear solution, and the resulting deep red solution was allowed to warm to ambient temperature over 1 h. The reaction mixture was poured onto iced water and extracted with dichloromethane. The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated to a dirty white solid. Flash column chromatography on silica gel (230-400 mesh) using 6% ethyl acetate in hexane as the eluent afforded the title compound as a white solid (0.177 g, 67%).

Provenance & Evidence