Benzyl Bromide → 6-Benzyloxynaphthalene-2-carboxylic acid methyl ester

Participants

Reaction Steps

Treat 6-hydroxynaphthalene-2-carboxylic acid methyl ester (4.77 g, 23.6 μmmol) and benzyl bromide (3.3 mL, 28.3 mmol) in DMF (22 mL) with cesium carbonate (15.3 g, 47.2 mmol). Stir the mixture for 22 h at RT and concentrate. Dilute the concentrate with EtOAc (300 mL) and water (100 mL). Wash the organic layer with brine (3×100 mL), dry it over Na2SO4, and filter. Concentrate the filtrate. Purify the product using medium pressure silica gel chromatography (15:85 to 50:50 EtOAc:hex) to give the title compound as a white solid (5.75 g, 83%). MS (ES) m/e 293 (M+1).

Provenance & Evidence