tert-butyl(chloro)dimethylsilane (Aldrich)

4-Bromophenol (Aldrich)

Imidazole  (Aldrich)

Dimethylformamide (Aldrich)

4-Bromophenol and imidazole were dried in a dessicator over P₂O₅. tert-Butyl(chloro)dimethylsilane (15.0 g, 0.1 mol) was added to a solution of 4-bromophenol (12.1 g, 0.07 mol) and imidazole (16.5 g, 0.24 mol) in dimethylformamide (50 cm³) and the mixture was magnetically stirred (2 d). Water (5 cm³) and 60/80 petrol (50 cm³) were then added, followed after 1 h by more water (100 cm³). The phases were separated and the aqueous phase extracted twice with 1: 1 60/80 petrol-diethyl ether (100 cm³). The combined organic phases were washed successively with water, aqueous NaOH solution (1 M), water and saturated NaCl solution and dried (MgSO₄). The solution was evaporated and the residue distilled to give a colourless oil, 19.8 g (98%), b.p. 67-68 ºC/0.01 mm.

δ_H  (CDCl₃, 60 MHz), 7.13d (2 H), 6.25d (2H), 0.93s (9 H), 0.16s (6 H).

δ_C (CDCl₃, 100 MHz), 154.78, 132.26, 121.68, 113.60, 25.61, 18.16, -4.50.

Riley PA, Cooksey CJ, Johnson CI, Land EJ, Latter AM, Ramsden CA., Eur J Cancer, 1997, 33(1), 135-143. PubMed PMID: 9071913. doi: 10.1016/S0959-8049(96)00340-1