Triethylamine → Acetophenone

Participants

Reaction Steps

Into a 500 mL single-neck flask fitted with a stirrer and thermometer, 10.0 g. of 4′-iodoacetophenone, 1.0 g. of PdCl2(dppf), and 17 mL triethylamine were placed in Dioxane (160 mL) and stirred at room temperature under a nitrogen atmosphere. This solution was then degassed with nitrogen for 15 minutes, followed by the addition of 8.8 mL pinacol borane syringe wise. Addition was exothermic and the solution turned dark immediately. The reaction was then heated at 85° C. for 6 h. The mixture was then cooled to room temperature and poured into H2O and the desired product was extracted with ether. This organic layer was washed with H2O, dried over MgSO4, and concentrated under reduced vacuum to yield a white solid. This material was purified via silica gel chromatography employing the Water's prep. 2000 and eluting with hexane/ethyl acetate 19:1 to yield intermediate title compound, acetophenone derivative, (6.4 g, 64%) as a white powder.

Provenance & Evidence