Synthesis and NMR Characterization of Halomethyl-Substituted Silanes

Tetrahydrofuran, 1,2-dimethoxyethane and diglyme were dried and distilled from sodium/benzophenone under Ar. Reagents were used as supplied without purification unless stated otherwise. All operations were performed under argon using Schlenk techniques unless stated otherwise. Sodium hydride (60% oil dispersion) was washed with hexane three times under Ar before use. (Trifluoromethyl)trimethylsilane was purchased from Oakwood Chemical (Estill, SC, USA). (Difluoromethyl)trimethylsilane [23 (link)], (bromodifluoromethyl)trimethylsilane [24 (link)], (chlorodifluoromethyl)trimethylsilane [25 (link)], (tribromomethyl)trimethylsilane [26 ] and (trichloromethyl)trimethylsilane [27 (link)] were prepared according to reported procedures. ¹H, ¹¹B and ¹⁹F NMR spectra were recorded on Bruker Avance-III 300 MHz instrument in CDCl₃ or CDC₃N. Chemical shifts are reported in ppm.