The general procedure for the synthesis of 1,4-bis(vinyl dimethylsilyl)benzene from dimethyl vinyl chlorosilane and 1,4-dibromobenzene was as follows: 1.28 g (52.5 mmol) of magnesium was added to a dry flask. Subsequently, a solution of 6.59 g (25 mmol) of 1,4-dibromobenzene dissolved in 20 mL of freshly distilled tetrahydrofuran (THF) was added slowly and dropwise over a period of 2 hours. The reaction mixture was heated to 40°C and stirred continuously for 2 hours. After the reaction mixture was cooled to room temperature, a solution of 6.65 g (55 mmol) of dimethylvinylchlorosilane dissolved in 15 mL of freshly distilled THF was slowly added over a period of 1 hour at ambient temperature. After that, the reaction mixture was heated to 40°C again and stirred for 2 hours. After completion of the reaction, the mixture was allowed to stand overnight and subsequently poured into distilled water. The aqueous phase was extracted with petroleum ether (30 mL x 3). The organic layers were combined and dried with anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was purified by column chromatography (using petroleum ether as eluent) to give 2.57 g (8% yield) of the target product 1,4-bis(vinyl dimethylsilyl)benzene.
