1.1: KNO3; H2SO4 2.1: Fe / acetic acid; ethyl acetate; H2O / 1 h / Heating 2.2: 86 percent / NaHCO3 / 0.17 h / Heating 3.1: HNO2; HCl 3.2: KI; CuI View Scheme

1.1: Fe / acetic acid; ethyl acetate; H2O / 1 h / Heating 1.2: 86 percent / NaHCO3 / 0.17 h / Heating 2.1: HNO2; HCl 2.2: KI; CuI View Scheme

1: With hydrogenchloride; HNO2 Sandmeyer reaction; 2: With copper(l) iodide; potassium iodide Sandmeyer reaction;

1: copper(l) iodide / N,N-dimethyl-formamide / 18 h / 100 °C 2: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / 3 h / 65 °C 3: hydrazine / ethanol / 18 h / 60 °C 4: trichlorophosphate; N,N-dimethyl-formamide / 2 h / 100 °C View Scheme

1: Br2 / CCl4 / Heating; irradiation 2: water / Heating View Scheme