1: 1.) NaNO2, HCl, 2.) KI / 1.) H2O, 0 deg C, 2.) H2O, RT, 16 h 2: SOCl2 / toluene / 1 h / 110 °C 3: toluene / 2 h / 110 °C View Scheme

1: SOCl2 / toluene / 1 h / 110 °C 2: toluene / 2 h / 110 °C View Scheme

1: 87 percent / HNO3, H2SO4 / 3 h / 0 - 20 °C 2: 76 percent / H2 / 10percent Pd/C / ethanol / 24 h / 760 Torr / Ambient temperature 3: 1.) NaNO2, HCl, 2.) KI / 1.) H2O, 0 deg C, 2.) H2O, RT, 16 h 4: SOCl2 / toluene / 1 h / 110 °C 5: toluene / 2 h / 110 °C View Scheme

1: 76 percent / H2 / 10percent Pd/C / ethanol / 24 h / 760 Torr / Ambient temperature 2: 1.) NaNO2, HCl, 2.) KI / 1.) H2O, 0 deg C, 2.) H2O, RT, 16 h 3: SOCl2 / toluene / 1 h / 110 °C 4: toluene / 2 h / 110 °C View Scheme

in benzene 4 h; Heating;