Tetrahydrofuran → Silane, (chloromethyl)(4-ethoxyphenyl)dimethyl-

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A mixture of 60 ml of THF, p-bromophenetole (9.7 gram) and chloromethyldimethylsilyl chloride (7.3 gram) was cooled in a dry ice/acetone bath. To the mixture was dropwise added 33 ml of 1.55M n-butyl lithium under an argon atmosphere. After stirring the mixture for additional 15 minutes at -78° C., the stirring was continued at room temperature for 30 minutes. The mixture was added with 6 ml of ethyl acetate and 30 ml of water, and extracted with ethyl ether. The ether extract was washed with saturated sodium chloride solution, dried, and concentrated. Distillation of the residue gave 5.5 gram of chloromethyldimethyl(4-ethoxyphenyl)silane. Physicochemical data of the product is listed in Table 3.

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