In a two-necked round-bottomed flask (RBF) equipped with a magnetic stirrer, triethylamine (TEA, 200 mL) was added and 1-bromo-4-iodobenzene (24.00 g, 84.83 mmol) was added at room temperature and protected by nitrogen. After stirring the mixture for 5 min, ethynyltrimethylsilane (13.19 mL, 93.31 mmol), dichlorobis(triphenylphosphine)palladium(II) (Pd(PPh3)2Cl2, 2.98 g, 4.24 mmol), and cuprous iodide (CuI, 1.62 g, 8.48 mmol) were added sequentially. The reaction mixture was continued to be stirred at the same temperature for 30 min. Subsequently, the excess TEA was removed by vacuum evaporation and the pH was adjusted to 1 by adding 1 N hydrochloric acid. extraction was carried out with ethyl acetate (EtOAc) and water, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate (MgSO4). After evaporation of the solvent, the residue was purified by column chromatography (eluent: hexane) to afford the target compound (4-bromophenyl ethynyl)trimethylsilane (21.00 g, 98% yield) as a white solid.1H NMR (CDCl3, 500 MHz): δ 7.19-7.06 (4H, m, ArH), 0.00 (9H, s, Si(CH3)3); 13C NMR (CDCl3, 125 MHz): δ 133.5, 131.6, 122.8, 122.3, 104.0, 95.7, 0.00.
silane pictures](https://img.chemicalbook.com/ProductImageEN/2019-12/Small/3834badd-f26f-4227-9148-3a2815d2fd7b.png)