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

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-2-naphthol (3.00 g, 13.5 mmol) in 67 ml of methylene chloride were added 4-dimethylaminopyridine (0.164 g, 1.34 mmol) and t-butyldimethylsilyl chloride (2.64 g, 17.5 mmol). The solution was cooled to 0° C. and triethylamine (2.60 ml, 18.7 mmol) was added. After 1.5 hours the reaction mixture was diluted with ethyl acetate and washed successively with saturated NH4Cl, H2O, and brine. Drying (MgSO4), evaporation, and purification by flash chromatography through 130 g of silica gel (1:4 CH2Cl2 /hexane) yielded 3.83 g (85%) of the title compound.

Provenance & Evidence