1: 100 percent / imidazole / dimethylformamide / 20 °C 2: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 3: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 4: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 5: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 6: 52 percent / CuI / tetrahydrofuran / -26 °C 7: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

1: 100 percent / imidazole / dimethylformamide / 20 °C 2: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 3: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 4: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 5: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 6: 52 percent / CuI / tetrahydrofuran / -26 °C 7: 89 percent / aq. HCl / methanol / 44 h / 20 °C 8: 18 percent / H2 / Wilkinson's catalyst / ethanol View Scheme

hydrogenchloride in 1,4-dioxane; dichloromethane 0.166667 h;