1-Bromo-4-(difluoromethoxy)benzene → HCID 59305326, compound

Participants

Reaction Steps

In a 0.5-2 ml Biotage conical microwave vial equipped with magnetic spin vane was dissolved 4-(5-ethynyl-2-fluorophenyl)morpholine (540 mg, 1.50 mmol) in triethylamine (1.5 mL). Copper iodide (54 mg, 0.283 mmol) and Tetrakis(triphenylphosphine) palladium (105 mg, 0.091 mmol) were added. Lastly 1-bromo-4-(difluoromethoxy)benzene (0.750 g, 3.36 mmol) was added, the vial was covered with a teflon septa, an aluminum cap was crimped in place, and the assembly was set on a Biotage Emrys microwave instrument to irradiate at 80° C. for 30 minutes. The crude reaction was diluted with diethylether, washed with saturated ammonium chloride, and purified via column chromatography on a Yamazen W-Prep 2XY using 25% EtOAc in hexanes. Concentration by rotary evaporation afforded 500 mg of oil (96%); 1H NMR (400 MHz, DMSO-d6) δ ppm 3.03 (t, J=4.6 Hz, 4H) 3.73 (t, J=4.6 Hz, 4H) 7.13-7.14 (m, 1H) 7.16 (d, J=2.6 Hz, 1H) 7.17-7.19 (m, 2H) 7.22 (d, J=8.8 Hz, 2H) 7.24 (t, J=73.8 Hz, 1H) 7.60 (d, J=8.8 Hz, 2H); MS (ES) m/z 348.2 [M+H]+

Provenance & Evidence