1: NaOEt / ethanol; diethyl ether / 48 h / Ambient temperature 2: 48percent HBr / H2O / 4 h / 120 - 150 °C 3: 54 percent / LiNH2, Fe(NO3)3 / tetrahydrofuran; NH3 / 20 h 4: H2 / PtO2 / diethyl ether 5: pyridine / 0 °C 6: NaI / acetone / 2 h / Heating View Scheme

1: 54 percent / LiNH2, Fe(NO3)3 / tetrahydrofuran; NH3 / 20 h 2: H2 / PtO2 / diethyl ether 3: pyridine / 0 °C 4: NaI / acetone / 2 h / Heating View Scheme

1: 48percent HBr / H2O / 4 h / 120 - 150 °C 2: 54 percent / LiNH2, Fe(NO3)3 / tetrahydrofuran; NH3 / 20 h 3: H2 / PtO2 / diethyl ether 4: pyridine / 0 °C 5: NaI / acetone / 2 h / Heating View Scheme

1: H2 / PtO2 / diethyl ether 2: pyridine / 0 °C 3: NaI / acetone / 2 h / Heating View Scheme

sodium iodide in acetone 2 h; Heating; Yield given;

1: pyridine / 0 °C 2: NaI / acetone / 2 h / Heating View Scheme

1: 85 percent / hexamethylphosphoric acid triamide / 0.5 h / 0 °C 2: 92 percent / diethyl ether / 12 h / 0 - 5 °C 3: 1.) (n-Bu)3SnH, azobisbutyronitrile, 2.) iodine monochloride / 1.) toluene, reflux, 6 h, 2.) CCl4 4: 67 percent / 1 N aq. NaOH / ethanol / 1 h / Heating View Scheme