1: 93 percent / aq. NaN3 / dimethylformamide / 6 h / 110 °C 2: 93 percent / aq. Na2S / methanol / 24 h / 55 °C 3: 87 percent / aq. NaHCO3 / toluene / 16 h / Ambient temperature 4: 89 percent / Ph3P, Br2, Et3N / CH2Cl2 / 3 h / Ambient temperature 5: 99 percent / CuCl / 1 h / Ambient temperature View Scheme

hydrogenchloride in methanol; water; N,N-dimethyl-formamide

Yield given. Multistep reaction;

1: 93 percent / aq. NaN3 / dimethylformamide / 6 h / 110 °C 2: 93 percent / aq. Na2S / methanol / 24 h / 55 °C View Scheme

sodium hydride in N,N-dimethyl-formamide 1.) 40 min, room temperature, 2.) 100 deg C, 18 h;