Hydrochloric Acid → Chloromethyl-dimethyl(4-fluorobenzyl)silane

Participants

Reaction Steps

To the 4-fluorobenzylmagnesiumchloride, prepared from parafluorobenzylchloride (1.59 g, 11 mmol) and magnesium (0.25 g, 11 mmol) in ether (20 ml), was added dropwise, at 0° C., chloro-chloromethyl-dimethylsilane (1.43 g, 10 mmol )in ether (5 ml). Then the mixture was refluxed 6 hours, cooled to 0° C., hydrolyzed with 3N HCl (20 ml) and extracted with ether. The ether solution was washed with water, brine, dried and evaporated. Chromatography (silica gel, hexane) afforded chloromethyl-dimethyl-4-fluorobenzyl silane as an oil (2.01 g, 93% yield) 1H NMR, CDCl3, TMS) δ: 0.20 (s,6H), 2.27 (s,2H), 2.63 (s,2H), 6.90-7.13 (m,4H).

Provenance & Evidence