Benzyl Bromide → Methyl 7-(benzyloxy)naphthalene-2-carboxylate

Participants

Reaction Steps

Treat a solution of 7-hydroxynaphthalene-2-carboxylic acid methyl ester (2.84 g, 14.0 mmol) and benzyl bromide (1.84 mL, 15.5 mmol in DMF (14 mL) with cesium carbonate (9.10 g, 27.9 mmol). Stir the mixture for 2 h and concentrate. Dissolve the crude residue in EtOAc (150 mL) and 1 N HCl (50 mL). Wash the organic layer with brine (3×100 mL), dry over Na2SO4, and filter. Concentrate the filtrate and purify using medium pressure silica gel chromatography (10:90 EtOAc:hex) to give the title compound as a white solid (1.47 g, 36%). MS (ES) m/e 293 (M+1).

Provenance & Evidence