1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.25 h / 0 °C / Inert atmosphere 2: bromine; triphenylphosphine / dichloromethane / 4 h / 20 °C / Inert atmosphere 3: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4: hydrogen / methanol / 3 h / 20 °C / 3102.97 Torr View Scheme

1: toluene-4-sulfonic acid / tetrahydrofuran / 0.25 h / Reflux; Inert atmosphere 2: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 3: palladium diacetate; potassium carbonate; triphenylphosphine / N,N-dimethyl-formamide / 7 h / 120 °C / Inert atmosphere 4: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 20 °C / Inert atmosphere 5: hydrogen; palladium(II) oxide hydrate / methanol / 4 h / 3102.97 Torr View Scheme

1: toluene-4-sulfonic acid / tetrahydrofuran / 0.25 h / Reflux; Inert atmosphere 2: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 3: palladium diacetate; potassium carbonate; triphenylphosphine / N,N-dimethyl-formamide / 7 h / 120 °C / Inert atmosphere 4: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 20 °C / Inert atmosphere View Scheme