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

Participants

Reaction Steps

To a solution of 6-bromo-2-napthol (1.12 g, 5 mmol) in anhydrous THF (15 mL) was added imidazole (0.476 g, 7 mmol) followed by TBSCl (1.05 g, 7 mmol) at room temperature under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 40 h and was diluted with ether, washed with brine and dried over anhydrous Mg2SO4. The solvent was removed to yield the crude product, which was recrystallized from methanol. Yield: 1.36 g (80%), white crystals. 1H-NMR (CDCl3) □ 0.08 (s, 6H), 1.06 (s, 9H), 7.08 (dd, 1H), 7.15 (s, 1H), 7.47 (dd, 1H), 7.56 (d, 1H), 7.64 (d, 1H), 7.92 (s, 1H).

Provenance & Evidence