Imidazole → 1-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-4-iodobenzene

Participants

Reaction Steps

A solution of t-butyl-dimethylsilyl chloride (3.0 g) in dichloromethane (10 ml) was added dropwise to a stirred solution of 4-iodophenol (4.4 g) and imidazole (1.4 g) in dichloromethane (90 ml) whilst maintaining the temperature between 10° C. and 5° C. After the addition was complete, the reaction mixture was stirred for a further 4 hours at ambient temperature. The reaction mixture was washed with water, dried (MgSO4), and evaporated to give 4-(t-butyldimethylsilyloxy)iodobenzene as a colourless oil (6.4 g) NMR(DMSO-d6): 0.0(6H,s), 0.8(9H,s), 6.49-6.58(2H,d), 7.35-7.44(2H,d); m/z=334 (M).

Provenance & Evidence