1,2-dichloro-benzene T=170°C; 0.5 h;

1: 98 percent / H2, 1.5percent aq. NaOH / 10percent Pd/C / 40 °C / 760 Torr 2: 1.) NaNO2, 1.5percent aq. NaOH, conc. HCl, 2.) NaN3 / 1.) -10 deg C, 30 min, 2.) water, from -10 deg C to RT 3: 98 percent / SOCl2, pyridine / CHCl3 / 1.5 h / Heating 4: 98 percent / CH2Cl2 / 0.5 h / Ambient temperature 5: 81 percent / o-dichlorobenzene / 0.5 h / 170 °C View Scheme

in dichloromethane; acetone 0.5 h; Ambient temperature;

1: 1.) NaNO2, 1.5percent aq. NaOH, conc. HCl, 2.) NaN3 / 1.) -10 deg C, 30 min, 2.) water, from -10 deg C to RT 2: 98 percent / SOCl2, pyridine / CHCl3 / 1.5 h / Heating 3: 98 percent / CH2Cl2 / 0.5 h / Ambient temperature 4: 81 percent / o-dichlorobenzene / 0.5 h / 170 °C View Scheme

1: 98 percent / CH2Cl2 / 0.5 h / Ambient temperature 2: 81 percent / o-dichlorobenzene / 0.5 h / 170 °C View Scheme

1: 98 percent / SOCl2, pyridine / CHCl3 / 1.5 h / Heating 2: 98 percent / CH2Cl2 / 0.5 h / Ambient temperature 3: 81 percent / o-dichlorobenzene / 0.5 h / 170 °C View Scheme