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

Participants

Reaction Steps

tert-Butyldimethylsilyl chloride (1.8 g) was added over 30 minutes to a stirred solution of 4-bromo-4'-hydroxybiphenyl (2.49 g) and imidazole (1.63 g) in dimethylformamide (15 ml) whilst keeping the temperature of the reaction mixture below 10° C. The reaction mixture was stirred at room temperature for 18 hours. Diethyl ether (225 ml) was added, the ether washed with saturated sodium hydrogen carbonate solution (3×60 ml) and brine (100 ml), dried (MgSO4) and evaporated to yield, as a colourless oil, 4-bromo-4'-(tert-butyldimethylsilyloxy)biphenyl (3.2 g); NMR (CDCl3): 0.2(6H, s), 1.0(9H, s), 6.8-6.9(2H, d), 7.3-7. 4(4H, m) and 7.45-7.55(2H, d).

Provenance & Evidence