Imidazole → (3-Bromophenoxy)tri(propan-2-yl)silane

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromophenol (1.00 g, 5.78 mmol), and imidazole (984 mg, 14.45 mmol) in 6 mL of DMF was cooled to 0° C. and triisopropylsilyl chloride (922 μL, 6.94 mmol) was added and the solution was stirred for 24 hours. The reaction mixture was quenched with 10 mL H2O and 5 mL saturated aqueous NaHCO3. The aqueous layer was extracted with ether (3×10 mL), the pooled organic extracts were washed with brine, dried (MgSO4), and concentrated. The resulting oil was flash chromatographed on silica gel with hexanes to yield 209 (1.50 g, 79%). 1H NMR (CDCl3) δ 1.09 (d, J=7.2 Hz, 18H), 1.17-1.30 (m, 3H), 6.75-6.81 (m, 1H), 7.00-7.10 (m, 3H); 13C NMR (CDCl3) 156.89, 130.26, 124.14, 123.29, 122.5, 118.47.

Provenance & Evidence