Hydrochloric Acid → Silane, (chloromethyl)(4-ethoxyphenyl)dimethyl-

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To a mixture of 5.1 g (0.21 mole) of powdered magnesium metal in 100 ml of dry tetrahydrofuran was added dropwise 40 g (0.20 mole) of ethyl 4-bromophenyl ether. Upon completion of addition this mixture was heated at reflux for one hour. In a second flask was placed 28.5 g (0.199 mole) of (chloromethyl)dimethylchlorosilane in 100 ml of tetrahydrofuran, and this flask was cooled to -78° C. The contents of the first flask were added dropwise to the second flask. The temperature of the reaction mixture was maintained at -78° C. for one hour after addition was complete, and it was then poured into 200 ml of 10% hydrochloric acid. The organic phase was washed once with 10% hydrochloric acid. The aqueous phase was extracted with diethyl ether, and these extracts were combined with the organic phase. After being dried, filtered, and having the solvent evaporated under reduced pressure, the residue was vacuum distilled, yielding 10.5 g of (chloromethyl)(4-ethoxyphenyl)dimethylsilane, b.p. 99°-110° C./0.12 mm of Hg. The nmr spectrum was consistent with the proposed structure.

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