bromine; dibenzoyl peroxide in 1,1,2,2-tetrachloroethylene 20 h; HeatingIrradiation;

1: 1.) anhydrous aluminum chloride, sodium chloride, 2.) hydrochloric acid / 1.) 190 deg C, 2 min, 2.) heating, 2 h 2: 82.5 percent / bromine, benzoyl peroxide / tetrachloroethene / 20 h / Heating; Irradiation View Scheme

1: 1.) anhydrous aluminum chloride, sodium chloride, 2.) hydrochloric acid / 1.) 190 deg C, 2 min, 2.) heating, 2 h 2: 82.5 percent / bromine, benzoyl peroxide / tetrachloroethene / 20 h / Heating; Irradiation View Scheme

bromine

1: 69.2 percent / sodium iodide / N,N-dimethyl-acetamide / 0.5 h / 65 - 70 °C 2: 55.6 percent / anhydrous potassium carbonate / dimethylformamide; butan-2-one / 1.5 h / Heating View Scheme

1: 69.2 percent / sodium iodide / N,N-dimethyl-acetamide / 0.5 h / 65 - 70 °C 2: 55.6 percent / anhydrous potassium carbonate / dimethylformamide; butan-2-one / 1.5 h / Heating 3: 55 percent / oxygen, triethyl phosphite, sodium tert-butoxide / 2-methyl-propan-2-ol; dimethylformamide / 1 h / -20 °C 4: 94 percent / aluminium chloride / benzene / 16 h / Ambient temperature View Scheme

acetic acid; sodium iodide 1.) dimethylacetamide, 70 deg C, 1 h, 2.) warming on a steam bath; Yield given. Multistep reaction. Yields of byproduct given;