1: 96 percent / aq. citric acid / tetrahydrofuran 2: 94 percent / triethylamine / dimethylformamide 3: 70 percent / NaBH4; LiCl / tetrahydrofuran; ethanol / 0 °C 4: 81 percent / triphenylphosphane; bromine; imidazole / CH2Cl2 / 2 h / 0 °C 5: 80 percent / ethanol; H2O / 6 h / Heating 6: aq. HCl; H2 / platinum oxide / propan-2-ol / 16 h / 2585.74 Torr View Scheme

1: 96 percent / aq. citric acid / tetrahydrofuran 2: 68 percent / NaBH4; LiCl / tetrahydrofuran; ethanol / 0 °C 3: 83 percent / triphenylphosphane; bromine; imidazole / CH2Cl2 / 3 h / 0 °C 4: 60 percent / aq. HCl / Heating View Scheme

1: 96 percent / aq. citric acid / tetrahydrofuran 2: 68 percent / NaBH4; LiCl / tetrahydrofuran; ethanol / 0 °C 3: 83 percent / triphenylphosphane; bromine; imidazole / CH2Cl2 / 3 h / 0 °C View Scheme

1: 96 percent / aq. citric acid / tetrahydrofuran 2: 94 percent / triethylamine / dimethylformamide 3: 70 percent / NaBH4; LiCl / tetrahydrofuran; ethanol / 0 °C 4: 81 percent / triphenylphosphane; bromine; imidazole / CH2Cl2 / 2 h / 0 °C View Scheme