1: 4.31 g / PBr3 / CHCl3 / 4 h / 0 °C 2: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 3: p-TsOH / ethanol / 3 h / Heating 4: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 5: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 6: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 2: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 3: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 2: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: p-TsOH / ethanol / 3 h / Heating 2: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 3: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 4: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 1.) KOH, 2.) H2, H2SO4 / 2.) 10percent Pd/C / 1.) ethanol, 1 h, reflux, 2.) ethanol, r.t. 2: 4.31 g / PBr3 / CHCl3 / 4 h / 0 °C 3: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 4: p-TsOH / ethanol / 3 h / Heating 5: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 6: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 7: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 81 percent / toluene-4-sulphonic acid / ethanol / 24 h / Heating 2: 1.) KOH, 2.) H2, H2SO4 / 2.) 10percent Pd/C / 1.) ethanol, 1 h, reflux, 2.) ethanol, r.t. 3: 4.31 g / PBr3 / CHCl3 / 4 h / 0 °C 4: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 5: p-TsOH / ethanol / 3 h / Heating 6: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 7: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 8: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme