Comparative studies on chlorination and methylation reactions have been carried out to afford chloromethyl(methyl)silanes. For chlorination reactions, three types of initiators, viz., azobisisobutyronitrile, benzoyl peroxide and dicumyl peroxide have been studied at different reaction conditions, e.g., solvent, temperature, time duration of reaction and molar ratio of reactants in view to get optimum yield of the products. The methylation reactions have also been carried out by diazomethane under PTC condition. The suitability of methylation and chlorination reaction has been evaluated to get pure and high yield of the products.