potassium carbonate in methanol; diethyl ether T=25°C; 16 h;

1: 81 percent / palladium(II) acetate, triphenylphosphine, copper(I) iodide, triethylamine / toluene / 4 h / 80 - 90 °C 2: 100 percent / anhydrous potassium carbonate / methanol; diethyl ether / 16 h / 25 °C View Scheme

1: 1.) NaNO2, conc. H2SO4, 2.) KI / 1.) 5 deg C, 30 min, 2.) H2O, 55 deg C, 1 h 2: 81 percent / palladium(II) acetate, triphenylphosphine, copper(I) iodide, triethylamine / toluene / 4 h / 80 - 90 °C 3: 100 percent / anhydrous potassium carbonate / methanol; diethyl ether / 16 h / 25 °C View Scheme

(i) PCl5, (ii) KOH, EtOH; Multistep reaction;