1: 1.) NaNO2, hydrogen chloride, 2.) KI 2: 99 percent / NaOMe / methanol View Scheme

1: 1.) NaNO2, HCl (2N) 2.) CuCl, HCl / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 30 min; 97 deg C, 5 min 2: 79 percent / aq. NaOH (40percent) / methanol / 0.25 h / Heating View Scheme

1: 1.) NaNO2, HCl (2N) 2.) CuCN, NaCN / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 1 h; 94 deg C, 5 min 2: 91.8 percent / aq. NaOH (40percent) / methanol / 0.17 h / Heating View Scheme

1: 1.)NaNO2, HCl / 1.) water and methanol, 5 deg C, 5 min, 2.) water, 97 deg C, 50 min 2: 74.9 percent / aq. NaOH (40percent) / methanol / 10 h / Heating View Scheme

1: 1.) NaNO2, HCl (2N) 2.) KI / 1.) water, 5 deg C, 15 min, 2.) water, room temp., 30 min; 85 deg C, 5 min 2: 20.9 percent / triphenylphosphine, triethylamine / palladium acetate / acetonitrile / 13 h / 110 - 115 °C View Scheme