1.1: NaIO4 / RuCl3 / acetonitrile; H2O / 0.08 h / 0 °C 2.1: LiBr / tetrahydrofuran; acetonitrile; H2O / 1 h / 25 °C 2.2: 1.00 g / H2SO4; H2O / diethyl ether / 5 h / 25 °C 3.1: 75 percent / 2,2'-azobis(isobutyronitrile); Bu3SnH / benzene / 3 h / 80 °C 4.1: PBr3; pyridine / diethyl ether / 51 h / -20 - 0 °C 4.2: dimethylformamide / 14 h / 70 °C 4.3: NiCl2*6H2O; NaBH4 / methanol / 1 h / 25 °C 5.1: aq. HCl / 16 h / 100 °C View Scheme

1.1: NaIO4 / RuCl3 / acetonitrile; H2O / 0.08 h / 0 °C 2.1: LiBr / tetrahydrofuran; acetonitrile; H2O / 1 h / 25 °C 2.2: 1.00 g / H2SO4; H2O / diethyl ether / 5 h / 25 °C 3.1: 75 percent / 2,2'-azobis(isobutyronitrile); Bu3SnH / benzene / 3 h / 80 °C 4.1: PBr3; pyridine / diethyl ether / 51 h / -20 - 0 °C 4.2: dimethylformamide / 14 h / 70 °C 4.3: NiCl2*6H2O; NaBH4 / methanol / 1 h / 25 °C 5.1: aq. HCl / 16 h / 100 °C View Scheme

With  thionyl chloride; triethylamine in  dichloromethane T=0°C; 0.5 h;