Propargyl alcohol → 3-[3-(Methyloxy)-4-nitrophenyl]-2-propyn-1-ol

Participants

Reaction Conditions

Reaction Steps

To 5-bromo-2-nitrophenyl methyl ether (4.0 g, 17.24 mmol) in 80 mL of acetonitrile was added, Bis(tri-t-butylphosphine)palladium(0) (0.253 g, 0.5 mmol), 2-propyn-1-ol (3.33 g, 59.4 mmol), and DABCO (4.44 g, 39.6 mmol). The mixture was heated to 60° C. for 1 h. The mixture was rotovaped down and then taken up in diethyl ether. The organic layer was washed with H2O, dried (Na2SO4), filtered, and rotovaped. The crude product was purified by flash chromatography to give the title compound of step A (1.7 g, 8.2 mmol, 41%). 1H NMR (400 MHz, CDCl3) δ ppm 7.80 (d, J=8.24 Hz, 1H), 7.12 (d, J=1.65 Hz, 1H), 7.06 (dd, J=8.33, 1.56 Hz, 1H), 4.52 (s, 2H), 3.94 (s, 3H).

Provenance & Evidence