Imidazole → (4-Bromo-2-ethylphenethoxy)(tert-butyl)dimethylsilane

Participants

Reaction Steps

Imidazole (2.1 g, 30.6 mmol) followed by tert-butylchlorodimethylsilane (2.5 g, 16.8 mmol) were added to a solution of 36B (3.5 g, 15.3 mmol) in CH2Cl2 (100 mL). The reaction mixture was stirred for 2 h then washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (0% to 30% EtOAc in hexanes) to yield 46A (4.3 g, 82%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm −0.02 (s, 6 H) 0.86 (s, 9 H) 1.20 (t, J=7.42 Hz, 3 H) 2.63 (q, J=7.51 Hz, 2 H) 2.79 (t, J=7.15 Hz, 2 H) 3.74 (t, J=7.15 Hz, 2 H) 7.22 (dd, J=7.97, 1.92 Hz, 1 H) 7.29 (d, J=2.20 Hz, 1 H).

Provenance & Evidence