1: 91 percent / SOCl2 / CHCl3 / 0.5 h / 0 °C 2: 44 percent / hexamethylphosphoamide / 1 h / 70 °C 3: NiCl2, NaBH4 / ethanol; dioxane; propan-2-ol / 5 h / 25 °C 4: hydrogen chloride, ethanol 5: 46 percent / sodium formate, formic acid / H2O / 4 h / 95 °C View Scheme

1: 94 percent / HBr / acetic acid / 1 h / 15 °C 2: 80 percent / tetrahydrofuran; ethanol; H2O / 1.5 h / Ambient temperature 3: aq. KOH / ethanol / 3.5 h / Heating 4: 88 percent / 30percent H2O2 / acetic acid / 1 h / Ambient temperature View Scheme

1: 94 percent / HBr / acetic acid / 1 h / 15 °C 2: 80 percent / tetrahydrofuran; ethanol; H2O / 1.5 h / Ambient temperature 3: aq. KOH / ethanol / 3.5 h / Heating 4: 97 percent / SOCl2 / benzene / 3 h / Heating 5: 64 percent / NH3 / CHCl3 / 1) 10 deg C, 1 h; 2) room temp., 3 h View Scheme

1: 94 percent / HBr / acetic acid / 1 h / 15 °C 2: 80 percent / tetrahydrofuran; ethanol; H2O / 1.5 h / Ambient temperature 3: aq. KOH / ethanol / 3.5 h / Heating View Scheme

With  hydrogen bromide in  acetic acid T=15°C; 1 h;   

Multi-step reaction with 4 steps 1: 94 percent / HBr / acetic acid / 1 h / 15 °C2: 80 percent / tetrahydrofuran; ethanol; H2O / 1.5 h / Ambient temperature3: aq. KOH / ethanol / 3.5 h / Heating4: 97 percent / SOCl2 / benzene / 3 h / Heating