1: 62 percent / Pd-black / 2 h / 280 - 300 °C 2: 1) Mg / 1) Et2O, 30 min 2) Et2O, 3h 3: P2O5, H3PO4 / 0.5 h / 60 - 70 °C 4: 86 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 5: 40 percent / Potassium nitrosodisulfonate, potassium hydrogen phosphate / acetone; H2O View Scheme

1: 62 percent / Pd-black / 2 h / 280 - 300 °C 2: 1) Mg / 1) Et2O, 30 min 2) Et2O, 3h 3: P2O5, H3PO4 / 0.5 h / 60 - 70 °C 4: 80 percent / pyridinium chlorochromate / CH2Cl2 / 96 h / Ambient temperature 5: 82 percent / NaBH4 / ethanol / 1 h / Ambient temperature 6: 42 percent / CH3SO2Cl, Et3N / CH2Cl2 / 0 °C 7: 77 percent / NaH, EtSH / dimethylformamide / 3 h / 150 °C 8: 57 percent / potassium nitrosodisulfonate, potassium hydrogen phosphate / H2O; acetone / 4 h View Scheme

Multi-step reaction with 6 steps 1: 62 percent / Pd-black / 2 h / 280 - 300 °C2: 1) Mg / 1) Et2O, 30 min 2) Et2O, 3h3: P2O5, H3PO4 / 0.5 h / 60 - 70 °C4: 80 percent / pyridinium chlorochromate / CH2Cl2 / 96 h / Ambient temperature5: 82 percent / NaBH4 / ethanol / 1 h / Ambient temperature6: 42 percent / CH3SO2Cl, Et3N / CH2Cl2 / 0 °C  

Multi-step reaction with 5 steps 1: 62 percent / Pd-black / 2 h / 280 - 300 °C2: 1) Mg / 1) Et2O, 30 min 2) Et2O, 3h3: P2O5, H3PO4 / 0.5 h / 60 - 70 °C4: 80 percent / pyridinium chlorochromate / CH2Cl2 / 96 h / Ambient temperature5: 82 percent / NaBH4 / ethanol / 1 h / Ambient temperature