Pyridine → ({4'-Bromo-[1,1'-biphenyl]-4-yl}oxy)(tert-butyl)dimethylsilane

Participants

Reaction Steps

To a 0° C. solution of 4-(4-bromophenyl)phenol (1.0 g, 4.0 mmol) and pyridine (0.65 mL, 8 mmol) in CH2Cl2 (20 mL) was added chloro-tert-butyldimethylsilane (0.72 g, 4.8 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 3 days, then diluted with water and extracted with CH2Cl2. The organic layer was washed with a 2N HCl solution, a 1N KOH solution, dried (MgSO4) and concentrated under reduced pressure to yield 1-(4-bromophenyl)-4-tert-butyldimethylsilyloxybenzene (0.89 g, 61%) as a white solid: TLC (33% EtOAc/hex) Rf 0.57.

Provenance & Evidence