hydrogen bromide T=150°C;

1: hydrogen; palladium 10 on activated carbon / methanol / 2 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 0 - 20 °C / |Inert atmosphere 3: hydrogen bromide / 5 h / 150 °C View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 0 - 20 °C / |Inert atmosphere 2: hydrogen bromide / 5 h / 150 °C View Scheme

n-butyllithium 1. diethyl ether, ice bath, 2h; 2. 20 degC, 12h; Yield given. Multistep reaction;