1: NaBH4 / propan-1-ol / 4 h / 30 - 35 °C 2: p-toluenesulfonic acid / toluene / Heating 3: H2 / 10percent Pd/C / ethanol 4: AlCl3 / 1,2-dichloro-ethane / 0.5 h 5: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C 6: SOCl2 / 1 h / Heating 7: 63 percent / pyridine / dimethyl ether / overnight View Scheme

1: NaBH4 / propan-1-ol / 4 h / 30 - 35 °C 2: p-toluenesulfonic acid / toluene / Heating 3: H2 / 10percent Pd/C / ethanol 4: AlCl3 / 1,2-dichloro-ethane / 0.5 h 5: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C 6: SOCl2 / 1 h / Heating 7: 25percent aq. NH4OH 8: 56 percent / SOCl2, dimethylformamide / 1.5 h / Ambient temperature View Scheme

1: NaBH4 / propan-1-ol / 4 h / 30 - 35 °C 2: p-toluenesulfonic acid / toluene / Heating 3: H2 / 10percent Pd/C / ethanol 4: AlCl3 / 1,2-dichloro-ethane / 0.5 h 5: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C View Scheme

1: NaBH4 / propan-1-ol / 4 h / 30 - 35 °C 2: p-toluenesulfonic acid / toluene / Heating View Scheme

1: NaBH4 / propan-1-ol / 4 h / 30 - 35 °C 2: p-toluenesulfonic acid / toluene / Heating 3: H2 / 10percent Pd/C / ethanol 4: AlCl3 / 1,2-dichloro-ethane / 0.5 h View Scheme

1: NaBH4 / propan-1-ol / 4 h / 30 - 35 °C 2: p-toluenesulfonic acid / toluene / Heating 3: H2 / 10percent Pd/C / ethanol 4: AlCl3 / 1,2-dichloro-ethane / 0.5 h 5: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C 6: SOCl2 / 1 h / Heating View Scheme

1: NaBH4 / propan-1-ol / 4 h / 30 - 35 °C 2: p-toluenesulfonic acid / toluene / Heating 3: H2 / 10percent Pd/C / ethanol View Scheme