Imidazole → ((4-Bromothiophen-2-yl)methoxy)(tert-butyl)diphenylsilane

Participants

Reaction Conditions

Reaction Steps

To a 250-mL round bottom flask fitted with a magnetic stir bar under a N2 atmosphere was added (4-bromothiophen-2-yl)methanol (2.0 g, 10 mmol, 1 equiv) and 30 mL of anhydrous DCM. The reaction mixture was then cooled to 0° C. and the tert-butyl-diphenylsilyl chloride (3.4 g, 3.2 mL, 12.4 mmol, 1.2 equiv) was added followed by imidazole (1.06 g, 15.5 mmol, 1.5 equiv). The reaction was stirred for 16 h and was allowed to equilibrate to rt. The reaction mixture was subsequently taken up in 75 mL DCM and washed with water (100 mL). The organic layer was then dried (Na2SO4), filtered, and evaporated in vacuo. The resulting residue was chromatographed over silica gel (0-10% EtOAc in heptane over 18 min.-retention time (tR) of product: 4-12 min) to give the desired ((4-bromothiophen-2-yl)methoxy)-tert-butyl diphenyl silane (4.3929 g, 98%). 1H-NMR (400 MHz, CD3CN) δ ppm 7.66-7.71 (m, 4H), 7.39-7.51 (m, 6H), 7.29 (d, J=1.46 Hz, 1H), 6.77-6.81 (m, 1H), 4.89 (d, J=0.93 Hz, 2H), 1.06 (s, 9H).

Provenance & Evidence