1: iron; acetic acid / methanol / 2 h / |Reflux; |Inert atmosphere 2: N-bromosuccinmide / acetonitrile / 4 h / 0 - 20 °C / |Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); cesium fluoride; copper(l) iodide / toluene / 110 °C / |Inert atmosphere 4: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 110 °C 5: ammonium cerium (IV) nitrate / acetonitrile; water / 0 °C 6: pyridine; bromine / chloroform / 8 h / 20 °C / |Darkness; |Inert atmosphere 7: sodium azide / N,N-dimethyl-formamide / 0 °C / |Inert atmosphere 8: hydrogen; palladium on activated charcoal / methanol; ethyl acetate View Scheme