in dimethyl sulfoxide 2 h;

1: With triphenylphosphine in dichloromethane T=20°C; Appel Halogenation; 0.166667 h; Inert atmosphere; 2: With carbon tetrabromide in dichloromethane T=-78°C; Appel Halogenation; 2 h; Inert atmosphere;

azobisisobutyronitrile in N-bromosuccinmide; water

hydrogen bromide; sodium bromide in chloroform; water T=5 - 15°C; Electrolysis;

1.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / |Inert atmosphere 2.1: triphenylphosphine / dichloromethane / 0.17 h / 20 °C / |Inert atmosphere 2.2: 2 h / -78 °C / |Inert atmosphere View Scheme

1.1: CH3BF3(1-)*H(1+)*C4H10O; N-bromosuccinmide / acetonitrile / 23 h / -10 - 20 °C / |Inert atmosphere 2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / |Inert atmosphere 3.1: triphenylphosphine / dichloromethane / 0.17 h / 20 °C / |Inert atmosphere 3.2: 2 h / -78 °C / |Inert atmosphere View Scheme

1.1: potassium carbonate / acetone / 4 h / |Inert atmosphere; |Reflux 2.1: CH3BF3(1-)*H(1+)*C4H10O; N-bromosuccinmide / acetonitrile / 23 h / -10 - 20 °C / |Inert atmosphere 3.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / |Inert atmosphere 4.1: triphenylphosphine / dichloromethane / 0.17 h / 20 °C / |Inert atmosphere 4.2: 2 h / -78 °C / |Inert atmosphere View Scheme

1: aqueous NaOH / 50 °C 2: aqueous HBr View Scheme