Silane, (chloromethyl)trimethyl- → o-Toluenesulfonyl chloride

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Reaction Steps

About 12.3 g (0.1 Mol) of commercially available chloromethyltrimethylsilane were dissolved in 100 ml of diethyl ether, and 2 ml of this solution were added under an inert gas to a mixture containing 3 g of magnesium turnings and one drop of ethyl iodide. After the reaction had been initiated by warming, the remainder of the silane/ether mixture was added dropwise at 20° C. with stirring over a period of one hour. When the addition was complete, the mixture was refluxed for an additional 30 minutes, then cooled and decanted from the excess magnesium. The resultant solution was added dropwise over a period of 30 minutes with stirring at 20° to 30° C. to a solution containing 22.7 g (0.1 Mol) of 2-(4-chlorophenyl)ethyl toluene sulfonate (obtained from commercially available 2-(4-chlorophenyl)ethanol by the known reaction with toluene sulfonyl chloride) in 100 ml of tetrahydrofuran. When the addition was complete, 100 ml of the solvent mixture were removed by distillation and replaced by 50 ml of tetrahydrofuran. The mixture was heated at an internal temperature of 60° C. for 60 minutes, during which time magnesium tosylate precipitated. After cooling, the mixture was poured over ice and acidified with a little hydrochloric acid, and the aqueous phase was extracted twice with tert-butyl methyl ether. The collected organic phases were washed with NaCl solution, dried and evaporated. About 17.1 g (75.4 percent yield) of 1-chloro-4-(1-trimethylsilylpropyl)benzene were obtained by fractional distillation of the residue at 16 hPa and at 115° to 118° C.

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