N-bromosuccinmide in N,N-dimethyl-formamide T=0 - 20°C; 0.5 h;

1: triethylamine / dichloromethane / 0.75 h / 0 - 20 °C 2: palladium 10 on activated carbon; hydrogen / ethyl acetate; ethanol / 3 h / 20 °C / 51683.5 Torr 3: N-bromosuccinmide / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C View Scheme

1: palladium 10 on activated carbon; hydrogen / ethyl acetate; ethanol / 3 h / 20 °C / 51683.5 Torr 2: N-bromosuccinmide / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 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

1.1: 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 View Scheme