1: phosphorus pentachloride / dichloromethane / 1 h / 0 - 5 °C 2: AlCl3, aluminium chloride / dichloromethane / 4 h / 3 - 8 °C 3: Pearlman's catalist; sulfuric acid; hydrogen; trifluoroacetic acid / 24 h / 20 °C / 5171.62 Torr 4: water; potassium hydroxide / methanol / 24 h / Reflux 5: bromine / water / 2 h / 0 - 5 °C View Scheme

1: phosphorus pentachloride / dichloromethane / 1 h / 0 - 5 °C 2: AlCl3, aluminium chloride / dichloromethane / 4 h / 3 - 8 °C 3: Pearlman's catalist; sulfuric acid; hydrogen; trifluoroacetic acid / 24 h / 20 °C / 5171.62 Torr 4: water; potassium hydroxide / methanol / 24 h / Reflux 5: ethanol; water / 1 h / 20 °C 6: acetic acid / 2 - 4 h / 100 °C 7: sodium tetrahydroborate / dichloromethane; water; isopropyl alcohol / 16 h / 20 - 25 °C View Scheme

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  

Stage #1: With  phosphorus pentachloride in  dichloromethane T=0 - 5°C; 7 h; Stage #2: With  AlCl3, aluminium chloride in  dichloromethane T=3 - 8°C; 7.5 h;  Show Experimental Procedure