Imidazole → 2-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthalene

Participants

Reaction Steps

To a solution of 6-bromo-2-naphthol (13.68 g, 61.33 mmol) and TBDMS-Cl (11.09 g, 73.6 mmol) in DMF (50 mL) was added imidazole (10.2 g, 150 mmol). The solution was stirred for 3 hr, mixed with sodium bicarbonate solution (250 mL), and extracted with 50% ethyl acetate-hexanes (3×250 mL). The combined organic layers were washed with water, dried over magnesium sulfate, filtered and evaporation of the solvent yielded a tan oil which was dried under vacuum to yield 19.92 g (97%) of the title compound as a white solid:

Provenance & Evidence