Tetrahydrofuran → Chloromethyl(4-fluorophenyl)divinylsilane

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To a solution of 6.3 ml (0.050 mol) of chloromethyltrichlorosilane in 75 ml of tetrahydrofuran cooled to -15° C. was added 25 ml of a 2.0 molar solution of p-fluorophenylmagnesium bromide (0.050 mol) at a rate that held the temperature below 0° C. The resulting suspension was stirred 30 minutes at 0° C. then allowed to warm to room temperature over 1 hour. A solution of vinylmagnesium bromide (71 ml, 1.4 molar in tetrahydrofuran) was then added, keeping the temperature below 35° C. The mixture was stirred 2 hours, then washed with saturated ammonium chloride. The aqueous layer was washed with ether-hexanes, and the combined organic layers were washed with brine, dried over sodium sulfate and evaporated. Kugelrohr distillation gave 7.25 g of the title compound as a colorless oil: nmr (CDCl3) 3.1 (2H, s), 5.8-6.7 (6H, m), 7.1, 7.7 (4H, two approximate t); ir (neat) 3060, 2955, 1590, 1497, 1402, 1232, 1162, 1105, 1006, 960, 821, 768 cm-1.

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