1: 88 percent / MgO, H2 / 10percent Pd/C / dioxane / 2585.7 Torr 2: 84 percent / H2 / Raney Ni / acetic acid / 2585.7 Torr 3: 89 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature 4: 90 percent / Heating 5: 83 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight 6: 80 percent / pyridine / 48 h / Ambient temperature 7: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 8: 50percent aq. MeOH / 4 h / Heating 9: HBr / dioxane / 20 h 10: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

With  thionyl chloride in  chloroform; N,N-dimethyl-formamide  Heating;   

Multi-step reaction with 4 steps 1: 88 percent / MgO, H2 / 10percent Pd/C / dioxane / 2585.7 Torr2: 84 percent / H2 / Raney Ni / acetic acid / 2585.7 Torr3: 89 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature4: 90 percent / Heating  

Multi-step reaction with 6 steps 1: 88 percent / MgO, H2 / 10percent Pd/C / dioxane / 2585.7 Torr2: 84 percent / H2 / Raney Ni / acetic acid / 2585.7 Torr3: 89 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature4: 90 percent / Heating5: 83 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight6: 80 percent / pyridine / 48 h / Ambient temperature