1: 276 mg / SOCl2 / CHCl3; dimethylformamide / Heating 2: 88 percent / MgO, H2 / 10percent Pd/C / dioxane / 2585.7 Torr 3: 84 percent / H2 / Raney Ni / acetic acid / 2585.7 Torr 4: 89 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature 5: 90 percent / Heating 6: 83 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight 7: 80 percent / pyridine / 48 h / Ambient temperature 8: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 9: 50percent aq. MeOH / 4 h / Heating 10: HBr / dioxane / 20 h 11: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

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

Multi-step reaction with 5 steps 1: 276 mg / SOCl2 / CHCl3; dimethylformamide / Heating2: 88 percent / MgO, H2 / 10percent Pd/C / dioxane / 2585.7 Torr3: 84 percent / H2 / Raney Ni / acetic acid / 2585.7 Torr4: 89 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature5: 90 percent / Heating  

Multi-step reaction with 7 steps 1: 276 mg / SOCl2 / CHCl3; dimethylformamide / Heating2: 88 percent / MgO, H2 / 10percent Pd/C / dioxane / 2585.7 Torr3: 84 percent / H2 / Raney Ni / acetic acid / 2585.7 Torr4: 89 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature5: 90 percent / Heating6: 83 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight7: 80 percent / pyridine / 48 h / Ambient temperature