1-(Difluoromethoxy)-4-ethynylbenzene → HCID 59305291, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(1-Fluoro-pent-4-enyl)-3-iodo-benzene (0.4 g, 1.38 mmol) in DMF (6 ml) were added TEA (0.96 ml, 6.9 mmol) and 1-Difluoromethoxy-4-ethynyl-benzene (0.233 g, 1.378 mmol). The reaction was degassed by bubbling argon through it for 5 minute and then dichlorbis(triphenylphospine)palladium (0.048 g, 0.069 mmol), and copper iodide (0.013 g, 0.693 mmol) were added simultaneously. The reaction mixture was heated at 65° C. for 15 min. cooled and quenched with 0.1 N HCl (15 ml). The aqueous was extracted with Et2O (3×15 ml). The combined organic extracts were washed with brine (20 ml), dried (MgSO4), and concentrated. The crude material was purified by chromatography (2.5%-5% Ethyl acetate/Petroleum Ether) to afford the titled compound (0.246 g, 54%) as a slight orange oil, identified by NMR and mass spectral analyses; MS (EI+): 330 (M+)

Provenance & Evidence