Ammonium Chloride → HCID 66764449, compound

Participants

Reaction Steps

Bis(triphenylphosphine)palladium(II) chloride (0.106 g, 0.151 mmol), copper(I) iodide (0.058 g, 0.303 mmol) and triphenylphospine (0.079 g, 0.303 mmol) are dissolved in a mixture of i-Pr2NH (11.36 ml)/DMF (3.79 ml) (degassed with N2 for 15 min). 2-(2-Bromo-4-(trifluoromethyl)phenyl)acetonitrile (1.1 g, 3.8 mmol) is added to the resultant orange solution. The mixture is stirred at RT for one hour. Triethyl(ethynyl)silane (1.018 ml, 5.68 mmol) is added dropwise, and the batch is warmed to 80° C. After 1 hour, a saturated, aqueous NH4Cl solution (50 ml) is added to the strongly dark-coloured batch. After phase separation, the aqueous phase is extracted three times with 50 ml of ethyl acetate each time. The combined organic phases are dried over Na2SO4 and evaporated to dryness in vacuo. The residue is purified by chromatography on silica gel with a 98:2 mixture of petroleum ether and ethyl acetate, giving 2-(2-((triethylsilyl)ethynyl)-4-(trifluoromethyl)phenyl)acetonitrile (orange oil, 91%, 1.226 g, 3.79 mmol);

Provenance & Evidence