sodium hydrogencarbonate in methanol; water 0.0833333 h; Heating;

1: 94.5 percent / NaHCO3 / methanol; H2O / 0.08 h / Heating 2: 95.1 percent / NaH(50percent) / dimethylformamide / 4 h 3: 92.5 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature 4: 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 5: 92.7 percent / aq. NaOH (40percent) / methanol / 0.17 h / Heating View Scheme

1: 94.5 percent / NaHCO3 / methanol; H2O / 0.08 h / Heating 2: 95.1 percent / NaH(50percent) / dimethylformamide / 4 h 3: 92.5 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature 4: 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 5: 79 percent / aq. NaOH (40percent) / methanol / 0.25 h / Heating View Scheme

1: 94.5 percent / NaHCO3 / methanol; H2O / 0.08 h / Heating 2: 95.1 percent / NaH(50percent) / dimethylformamide / 4 h 3: 92.5 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature 4: 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 5: 91.8 percent / aq. NaOH (40percent) / methanol / 0.17 h / Heating View Scheme

1: 94.5 percent / NaHCO3 / methanol; H2O / 0.08 h / Heating 2: 95.1 percent / NaH(50percent) / dimethylformamide / 4 h 3: 92.5 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature 4: 1.)NaNO2, HCl / 1.) water and methanol, 5 deg C, 5 min, 2.) water, 97 deg C, 50 min 5: 74.9 percent / aq. NaOH (40percent) / methanol / 10 h / Heating View Scheme

1: 94.5 percent / NaHCO3 / methanol; H2O / 0.08 h / Heating 2: 81.8 percent / NaH(50percent) / dimethylformamide; benzene / 17 h 3: 91.8 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature 4: 1.)NaNO2, HCl / 1.) water and methanol, 5 deg C, 5 min, 2.) water, 97 deg C, 20 min View Scheme

1: 94.5 percent / NaHCO3 / methanol; H2O / 0.08 h / Heating 2: 95.1 percent / NaH(50percent) / dimethylformamide / 4 h 3: 92.5 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature 4: 1.) NaNO2, HCl (2N) 2.) KI / 1.) water, 5 deg C, 15 min, 2.) water, room temp., 30 min; 85 deg C, 5 min 5: 20.9 percent / triphenylphosphine, triethylamine / palladium acetate / acetonitrile / 13 h / 110 - 115 °C View Scheme