1-(Difluoromethoxy)-4-ethynylbenzene → HCID 59305294, compound

Participants

Reaction Steps

To a CEM snap top microwave vial (10 ml) equipped with a magnetic stir bar (3×10 mm) was added 2-(3-bromobenzyl)furan (385 mg, 1.62 mmol) in triethylamine (1.5 mL). Copper iodide (80 mg, 0.40 mmol), Tetrakis(triphenylphosphine) palladium (140 mg, 0.121 mmol) and 1-(difluoromethoxy)-4-ethynylbenzene (0.270 mg, 1.60 mmol) were added at room temperature. The reaction was capped and irradiated in a CEM Explorer microwave at 80° C. for 30 minutes then forced air-cooled. The crude material was loaded onto silica gel. Purification by chromatography (2% EtOAc in hexanes) afforded 0.317 gm of an oil (61%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.99 (s, 2H) 6.16 (dd, J=3.1, 0.8 Hz, 1H) 6.37 (dd, J=3.1, 2.0 Hz, 1H) 7.21 (d, J=8.8 Hz, 2H) 7.28 (ddd, J=7.5, 1.6, 1.6 Hz, 1H) 7.31 (t, J=73.7 Hz, 1H) 7.34-7.42 (m, 3H) 7.53 (dd, J=1.9, 0.7 Hz, 1H) 7.61 (d, J=9.0 Hz, 2H); MS (EI) m/z 324.0 [M+·].

Provenance & Evidence