1: 29 percent / aluminum chloride / 11 h / 180 °C 2: 1.) gas HCl, 2.) sodium nitrite, conc. HCl / 1.) benzene, 2.) 0 - 5 deg C, 10 min 3: sodium azide / H2O / 0.17 h / 40 - 50 °C View Scheme

1: 29 percent / aluminum chloride / 11 h / 180 °C 2: 1.) gas HCl, 2.) sodium nitrite, conc. HCl / 1.) benzene, 2.) 0 - 5 deg C, 10 min 3: sodium azide / H2O / 0.17 h / 40 - 50 °C View Scheme

sodium azide 1.) diazotization in conc. HCl; Multistep reaction;

in acetonitrile Ambient temperatureIrradiation;