SYNTHESIS OF (CHLOROMETHYL)SILANES BY THE LOW-TEMPERATURE REACTION OF CHLOROSILANES AND INSITU GENERATED (CHLOROMETHYL)LITHIUM IN TETRAHYDROFURAN

The reaction between chlorosilanes and (chloromethyl)lithium, generated in situ from bromochloromethane and n-butyllithium, was used to synthesize (chloromethyl)silanes. The method is applicable to a wide variety of chlorosilanes and is particularly useful for silanes that contain such reactive bonds as Si-Si, Si-H, Si-vinyl, and Si-allyl. The corresponding (chloromethyl)silanes are generally prepared in high yield. The method may be extended successfully to bromomethylation and iodomethylation of chlorosilanes, and also to the chloromethylation of the other group 14 element (Ge, Sn, and Pb) halides.