Benzoyl Peroxide → Benzofuran, 5-(2-bromoethyl)-

Participants

Reaction Steps

A mixture containing 5-(2-bromoethyl)-2,3-dihydrobenzo[2,3-b ]furan (3 g--see Preparation 13), freshly recrystallised N-bromosuccinimide (2.37 g), benzoyl peroxide (0.03 g) and carbon tetrachloride was heated under reflux for 2 hours. On cooling to room temperature, water (100 ml) and sodium metabisulphite (1 g) were added, the layers were separated and the aqueous layer was extracted with dichloromethane (3×50 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with hexane containing toluene (5%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as an oil, yield 1.25 g.

Provenance & Evidence