Ethane → (4-Bromophenylethynyl)trimethylsilane

Participants

Reaction Steps

Dropwise over 30 minutes, 26.4 g of p-bromophenyl acetylene in solution in 100 ml of tetrahydrofuran were added to 215 ml of the magnesium compound solution prepared above and the reaction was lively and immediately was accompanied by an evolution of ethane and a rise in temperature. The temperature was brought back to 15°-20° C. and stirring was continued for 10 minutes. Over 5 minutes, 20 ml of chlorotrimethylsilane was added dropwise and after allowing the temperature to return to the ambient and stirring for 30 minutes, the reaction medium was diluted by the addition of 200 ml of a saturated aqueous solution of NH4Cl, followed by decanting and extracting with tetrahydrofuran. The extracts were washed with salted water, dried and concentrated to dryness by distilling under reduced pressure. The oily residue was taken up in 150 ml of methanol and crystallization was initated. The crystals were separated, washed and dried to obtain 18.67 g of p-bromophenylethynyl trimethylsilane melting at about 65° C.

Provenance & Evidence