1: With hydrogenchloride; sodium nitrite in water; acetonitrile T=0 - 5°C; Sandmeyer Reaction; 0.5 h; 2: With potassium iodide in water; acetonitrile T=20°C; Sandmeyer Reaction;

iodine; acetic anhydride; mercury(II) oxide in dichloromethane 14.5 h; Reflux; regiospecific reaction;

1.1: triethylamine / dichloromethane / 0.75 h / 0 - 20 °C 2.1: palladium 10 on activated carbon; hydrogen / ethyl acetate; ethanol / 3 h / 20 °C / 51683.5 Torr 3.1: N-bromosuccinmide / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 4.1: sulfuric acid / water; acetonitrile / 0.17 h / 0 °C 4.2: 1.5 h / 0 - 5 °C 4.3: 0.25 h / 0 °C 5.1: potassium hydroxide / methanol; dichloromethane / 1 h / 20 °C / |Inert atmosphere 6.1: potassium carbonate / acetone / 16 h / |Reflux View Scheme

1.1: palladium 10 on activated carbon; hydrogen / ethyl acetate; ethanol / 3 h / 20 °C / 51683.5 Torr 2.1: N-bromosuccinmide / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 3.1: sulfuric acid / water; acetonitrile / 0.17 h / 0 °C 3.2: 1.5 h / 0 - 5 °C 3.3: 0.25 h / 0 °C 4.1: potassium hydroxide / methanol; dichloromethane / 1 h / 20 °C / |Inert atmosphere 5.1: potassium carbonate / acetone / 16 h / |Reflux View Scheme

1.1: N-bromosuccinmide / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 2.1: sulfuric acid / water; acetonitrile / 0.17 h / 0 °C 2.2: 1.5 h / 0 - 5 °C 2.3: 0.25 h / 0 °C 3.1: potassium hydroxide / methanol; dichloromethane / 1 h / 20 °C / |Inert atmosphere 4.1: potassium carbonate / acetone / 16 h / |Reflux View Scheme

1.1: sulfuric acid / water; acetonitrile / 0.17 h / 0 °C 1.2: 1.5 h / 0 - 5 °C 1.3: 0.25 h / 0 °C 2.1: potassium hydroxide / methanol; dichloromethane / 1 h / 20 °C / |Inert atmosphere 3.1: potassium carbonate / acetone / 16 h / |Reflux View Scheme

1: potassium hydroxide / methanol; dichloromethane / 1 h / 20 °C / |Inert atmosphere 2: potassium carbonate / acetone / 16 h / |Reflux View Scheme

potassium carbonate in acetone 16 h; Reflux;

1.1: N-bromosuccinmide / N,N-dimethyl-formamide / 18.5 h / 0 - 20 °C / |Darkness 2.1: hydrogenchloride; sodium nitrite / acetonitrile; water / 0.5 h / 0 - 5 °C 2.2: 20 °C View Scheme

N-benzyl-N,N,N-triethylammonium chloride; palladium diacetate; sodium hydrogencarbonate in N,N-dimethyl-formamide T=40°C; Heck coupling; 24 h;