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

Participants

Reaction Steps

A solution of 6-bromonaphthalen-2-ol (5.0 g, 22.4 mmol) and imidazole (2.3 g, 33.6 mmole) in N,N-dimethylformamide (DMF) (5.0 mL) was added t-butyldimethylsilyl chloride (TBDMSCI) (3.7 g, 24.6 mmole) in one portion at 0° C. The mixture was allowed to warm to room temperature and stirred for 3 h. The reaction mixture was partitioned between EtOAc (500 mL) and water (300 mL). The aqueous layer was separated and extracted with EtOAc (2×100 mL) and the combined organic extracts were washed with brine (300 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (silica gel, hexanes) to afford (6-bromonaphthalen-2-yloxy)(tert-butyl)dimethylsilane (28, 7.4 g, 98%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.91 (d, J=1.8 Hz, 1H), 7.64 (d, J=8.7 Hz, 1H), 7.56 (d, J=8.7 Hz, 1H), 7.48 (dd, J=8.7, 1.8 Hz, 1H), 7.15 (d, J=2.4 Hz, 1H), 7.09 (dd, J=9.0, 2.4 Hz, 1H), 1.01 (s, 9H), 0.24 (s, 6H).

Provenance & Evidence