1: dimethylsulfoxide; benzene / 2 h 2: 92 percent / 4N NaOH / ethanol / 20 h / Heating 3: SOCl2 / benzene / 2 h / 50 - 60 °C 4: 91 percent / benzene; pyridine / 20 °C 5: 85 percent / POCl3 / toluene / 3 h / Heating 6: 100 percent / NaBH4 / methanol / 0.25 h 7: 75 percent / Pd(OAc)2; PPh3; K2CO3 / toluene / 26 h / Heating 8: 87 percent / LiAlH4 / tetrahydrofuran / 0.75 h / Heating View Scheme

hydrogenchloride in toluene 1 h; Heating;

acetic acid T=50 - 55°C;

1: 98 percent / NaBH4 / tetrahydrofuran; methanol / 2 h 2: SOCl2 / benzene / 20 °C View Scheme

1: 36 percent / Br2 2: 80 percent / K2CO3 / dimethylformamide / 0.08 h / Heating 3: NaBH4 / aq. ethanol / 1 h / 25 °C 4: 12 N aq. HCl View Scheme

1: 80 percent / K2CO3 / dimethylformamide / 0.08 h / Heating 2: NaBH4 / aq. ethanol / 1 h / 25 °C 3: 12 N aq. HCl View Scheme

1.1: dimethylsulfoxide; benzene / 2 h 2.1: 92 percent / 4N NaOH / ethanol / 20 h / Heating 3.1: SOCl2 / benzene / 2 h / 50 - 60 °C 4.1: 91 percent / benzene; pyridine / 20 °C 5.1: 85 percent / POCl3 / toluene / 3 h / Heating 6.1: 92 percent / methylene blue; O2 / CH2Cl2; methanol / 0.5 h / 15 °C / Irradiation 7.1: 82 percent / acetonitrile / 1.25 h / Heating 8.1: 92 percent / H2 / PtO2 / methanol / 3 h / 17 °C 9.1: 90 percent / NaBH4 / methanol / 2 h 10.1: CuCl2 / toluene / 0.03 h / 140 °C 10.2: NaBH4 / methanol / 2 h / 20 °C View Scheme

1: dimethylsulfoxide; benzene / 2 h 2: 92 percent / 4N NaOH / ethanol / 20 h / Heating 3: SOCl2 / benzene / 2 h / 50 - 60 °C 4: 91 percent / benzene; pyridine / 20 °C 5: 85 percent / POCl3 / toluene / 3 h / Heating 6: 92 percent / methylene blue; O2 / CH2Cl2; methanol / 0.5 h / 15 °C / Irradiation 7: 82 percent / acetonitrile / 1.25 h / Heating 8: 92 percent / H2 / PtO2 / methanol / 3 h / 17 °C 9: 81 percent / O2 / methanol / 1 h View Scheme