hydrogen bromide in acetic acid 24 h; Heating;

lithium aluminium tetrahydride in diethyl ether T=0°C;

1: LiAlH4 / diethyl ether / 0 °C 2: pyridinium p-toluenesulfonate / CH2Cl2 / 24 h / 20 °C View Scheme

N-bromosuccinmide; triphenylphosphine in N,N-dimethyl-formamide T=55°C; 0.5 h;

in tetrahydrofuran; methanol; hexane T=20°C; 2 h;

hydrogen; palladium on activated charcoal in tetrahydrofuran; methanol

1: 81 percent / hydrogen peroxide; ammonium heptamolybdate(VI) tetrahydrate / tetrahydrofuran; various solvent(s) / 20 °C 2: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran / -10 - 20 °C 3: 92 percent / hydrogen / palladium on carbon / methanol; tetrahydrofuran View Scheme

1: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran / -10 - 20 °C 2: 92 percent / hydrogen / palladium on carbon / methanol; tetrahydrofuran View Scheme

1: 92 percent / anhydrous potassium carbonate / acetone / 19 h / 20 - 40 °C 2: 81 percent / hydrogen peroxide; ammonium heptamolybdate(VI) tetrahydrate / tetrahydrofuran; various solvent(s) / 20 °C 3: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran / -10 - 20 °C 4: 92 percent / hydrogen / palladium on carbon / methanol; tetrahydrofuran View Scheme

1.1: p-toluenesulfonic acid / 24 h / Heating 2.1: methanesulfonyl chloride / CHCl3 / Heating 2.2: LiBr / acetone / Heating View Scheme