1: 92 percent / NaI / acetone / 12 h / Heating 2: 69 percent / dimethylsulfoxide / 1 h / Ambient temperature 3: 71 percent / NaBH4, H2, Ni(OAc)2, ethylenediamine / aq. ethanol / 2.5 h View Scheme

1: 81 percent / NaI / dimethylformamide / 3 h / 100 °C 2: 98 percent / H2, quinoline / Pd/BaSO4 / ethyl acetate 3: 11.9 g / KOH / ethanol; H2O / 12 h / 90 °C 4: 87 percent / BF3*Et2O / 5 h / 60 °C 5: 14.2 g / NEt3 / diethyl ether / 1) 0 deg C, 1 h, 2) r.t., 2 h 6: 12.6 g / sodium azide / dimethylformamide / 6 h / 65 °C View Scheme

1: 93 percent / dimethylsulfoxide / 1 h / 70 °C 2: 70 percent / aq. NaOH / ethanol / 18 h / Heating 3: 100 percent / diethyl ether / 0.08 h / 0 °C 4: 86 percent / H2, quinoline / Pd/BaSO4 View Scheme

1: 93 percent / dimethylsulfoxide / 1 h / 70 °C 2: 70 percent / aq. NaOH / ethanol / 18 h / Heating 3: 100 percent / diethyl ether / 0.08 h / 0 °C View Scheme

1: 93 percent / dimethylsulfoxide / 1 h / 70 °C 2: 70 percent / aq. NaOH / ethanol / 18 h / Heating 3: 100 percent / diethyl ether / 0.08 h / 0 °C 4: 86 percent / H2, quinoline / Pd/BaSO4 5: PPh3, Br2 / CH2Cl2 / 2.5 h / Ambient temperature View Scheme

in dimethyl sulfoxide T=70°C; 1 h;

1: 92 percent / NaI / dimethylformamide / 3 h / 100 °C 2: 78 percent / Hydrogen / Pd, BaSO4, quinoline / ethyl acetate 3: 89 percent / KOH / methanol; H2O / 19 h / Heating 4: 72 percent / CBr4, PPh3 / CH2Cl2 / 3 h / 0 - 25 °C View Scheme