thionyl chloride in dichloromethane 0.5 h;

thionyl chloride Hydrieren des Reaktionsprodukts an Palladium/Kohle in Methanol;

acetic anhydride in pyridine; water

1: 1.) NaH / 1.) DMF, -10 deg C, 30 min, 2.) DMF, -15 deg C, 30 min 2: 29 percent / H2O / 5 h / 150 °C 3: 58 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 4: 96 percent / 2N aq. HCl / methanol / 2 h / Heating 5: SOCl2 / CHCl3 / 1 h / Heating 6: dimethylformamide / 1 h / Ambient temperature 7: 65 percent / piperidine / ethanol / 18 h / Heating 8: 56 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide; tetrahydrofuran / 18 h / Ambient temperature 9: 72 percent / 4N aq. HCl / 18 h / Heating View Scheme

thionyl chloride in chloroform; toluene T=20 - 35°C; 1 h;

thionyl bromide in dichloromethane T=20°C; 3 h;

1: SOCl2 / 4 h / 20 °C 2: 1.8 g / dimethylsulfoxide / 1 h / 100 °C View Scheme