Water → N,N-Diethyl-2-(trifluoromethoxy)-4-vinylbenzamide

Participants

Reaction Steps

To a stirring degassed solution of N,N-diethyl-4-bromo-2-(trifluoromethoxy)benzamide (2373 mg, 7 mmol) in THF (40 mL) was added tetrakis(triphenylphosphine)palladium(0) (97 mg, 0.08 mmol). After 15 min., potassium carbonate (2898 mg, 21 mmol), 2,4,6-trivinylcyclotriboroxane pyridine complex (2663 mg, 7 mmol), and water (8 mL). The reaction was heated to reflux for 3 h and then cooled to room temperature. The reaction was diluted with brine and extracted with EtOAc (3×25 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a pale yellow oil. The oil was purified by flash chromatography (SiO2, 0-50% EtOAc in hexanes) to give 1783 mg of the desired product as a colorless oil. MS (ESI) 288 (M+H).

Provenance & Evidence