1: 84 percent / K2CO3 / dimethylformamide / 5 h / 20 °C 2: aq. HCl / dioxane / 24 h / 80 °C 3: 1.86 g / K2CO3 / dimethylformamide / 1 h / 60 °C 4: hydrogen / Pd/C / ethyl acetate; ethanol / 5 h / 20 °C / 760 Torr 5: 1.11 g / potassium nitrosodisulfonate / H2O; acetone / 3 h / 20 °C View Scheme

1: 87 percent / NaH; Bu4NI / tetrahydrofuran / 24 h / 20 °C 2: 84 percent / aq. HCl / methanol / 2 h / Heating 3: 73 percent / Cs2CO3 / acetonitrile / 1 h / -40 °C 4: 92 percent / NaH; Bu4NI / tetrahydrofuran / 24 h / 20 °C 5: 90 percent / KOH / methanol / 2 h / 50 °C 6: 97 percent / Cs2CO3 / acetonitrile / 24 h / 20 °C 7: 92 percent / H2 / Pd-C / ethyl acetate / 24 h / 20 °C 8: 92 percent / KOH / methanol / 1 h / 20 °C 9: aq. HCl / methanol / 3 h / Heating View Scheme