Dimethylformamide → 1-(Difluoromethoxy)-4-(phenylethynyl)benzene

Participants

Reaction Conditions

Reaction Steps

Into a mixture of ethynylbenzene (1.9 g, 18.5 mmol), 1-(difluoromethoxy)-4-iodobenzene (5 g, 18.5 mmol), N,N-dimethylformamide (35 mL), and triethylamine (12.8 mL, 92.6 mmol) was introduced anhydrous argon for 5 minutes. Then, copper(I) iodide (1.85 mmol, 351 mg) and dichlorobis(triphenylphosphine)palladium(II) (1.11, 0.71 g) were added into the mixture and the new mixture was stirred at 60° C. for 3 hours. The mixture cooled to room temperature, poured into water and extracted with ethyl ether. The organic extracts were dried over MgSO4. Evaporation and purification on silica gel (ISCO) using hexanes/EtOAc (100/1) as the eluting solvent, gave 1-(difluoromethoxy)-4-(phenylethynyl)benzene as a clear oil (3.45 g, 76% yield). MS m/e M+244; 1H NMR (400 MHz, DMSO-d6) δ 7.2 (d, J=8.78 Hz, 2H), 7.28-7.45 (m, 4H), 7.5-7.55 (m, 2H), 7.6 (d, J=7.78 Hz, 2H).

Provenance & Evidence