1: water; potassium hydroxide / methanol / 24 h / Reflux 2: bromine / water / 2 h / 0 - 5 °C View Scheme

1: water; potassium hydroxide / methanol / 24 h / Reflux 2: ethanol; water / 1 h / 20 °C 3: acetic acid / 2 - 4 h / 100 °C 4: sodium tetrahydroborate / dichloromethane; water; isopropyl alcohol / 16 h / 20 - 25 °C View Scheme

With  sulfuric acid; Pearlman's catalist; hydrogen; trifluoroacetic acid T=20°C; P=5171.62 Torr; 24 h;   

Multi-step reaction with 4 steps 1: sodium hydroxide / water / 1 h / 0 - 5 °C2: phosphorus pentachloride / dichloromethane / 1 h / 0 - 5 °C3: AlCl3, aluminium chloride / dichloromethane / 4 h / 3 - 8 °C4: Pearlman's catalist; sulfuric acid; hydrogen; trifluoroacetic acid / 24 h / 20 °C / 5171.62 Torr  

Multi-step reaction with 3 steps 1: phosphorus pentachloride / dichloromethane / 1 h / 0 - 5 °C2: AlCl3, aluminium chloride / dichloromethane / 4 h / 3 - 8 °C3: Pearlman's catalist; sulfuric acid; hydrogen; trifluoroacetic acid / 24 h / 20 °C / 5171.62 Torr