sodium hydroxide; bromine in 1,4-dioxane 1 h; Ambient temperature;

Multi-step reaction with 3 steps 1: 66 percent / AlCl3 / 1,2-dichloro-ethane / Heating; 1.) 2 h, reflux; 2.) 2 h, room temperature2: 93 percent / amalg. Zn, conc. HCl / acetic acid; toluene; H2O / 24 h / Heating3: 47 percent / AlCl3 / 1,2-dichloro-ethane / 12 h / Ambient temperature  

Multi-step reaction with 2 steps 1: 89 percent / NaBH4, trifluoroacetic acid / 24 h / Ambient temperature2: 47 percent / AlCl3 / 1,2-dichloro-ethane / 12 h / Ambient temperature