1,2-Dibromoethane → 1-{2-[4-(2-Bromoethoxy)naphthalen-1-yl]-1-benzofuran-3-yl}ethan-1-one

Participants

Reaction Steps

To a solution of 11.9 g. (0.039 mol.) of 3-acetyl-2-(4-hydroxynaphthyl)benzofuran in 400 ml. of 2-butanone was added 100 ml. (0.24 mol.) of 1,2-dibromoethane and 22 g. (0.16 mol.) of anhydrous potassium carbonate. The reaction mixture was refluxed for 8 hours, then the solvent was evaporated and the excess 1,2-dibromoethane was removed by distillation in vacuo. The residue was chromatographed on silica with 10% hexane in methylene chloride as eluant to give 3-acetyl-2-[4-(2-bromoethoxy)naphthyl]benzofuran, m.p. 115°-117°.

Provenance & Evidence