hydrogenchloride; iron in methanol; dichloromethane T=20°C; 0.25 h;

1.1: conc. sulfuric acid; aq. sodium nitrite / acetic acid / 0 °C 1.2: aq. sodium azide / 1 h / 20 °C 2.1: 810 mg / ethyl acetate / 2.5 h / Heating 3.1: 52 percent / triphenylphosphine / ethyl acetate / 1 h / Heating 4.1: 4.7 percent / conc. hydrochloric acid; iron powder / CH2Cl2; methanol / 0.25 h / 20 °C View Scheme

1: 810 mg / ethyl acetate / 2.5 h / Heating 2: 52 percent / triphenylphosphine / ethyl acetate / 1 h / Heating 3: 4.7 percent / conc. hydrochloric acid; iron powder / CH2Cl2; methanol / 0.25 h / 20 °C View Scheme