iodine; periodic acid in ethanol; water T=45°C; 0.0333333 h; microwave irradiation;

1: 95 percent / hydrogen / palladium on carbon / methanol; ethyl acetate / 20 °C 2: 94 percent / iodine; periodic acid / ethanol / 1 h / 40 °C View Scheme

1: 95 percent / H2 / Pd/C / methanol; ethyl acetate / 20 °C 2: 96 percent / I2; periodic acid / ethanol; H2O / 0.03 h / 45 °C / microwave irradiation View Scheme

1: 80 percent / K2CO3 / dimethylformamide / 0.5 h / 70 °C 2: KOH / ethanol / 0.75 h / 80 °C 3: 2.35 g / aq. HCl / CHCl3; methanol / 1 h / 40 °C 4: 530 mg / pyridine / 0.5 h / 70 °C 5: thallium(III) nitrate trihydrate / CHCl3 / 4 h / 30 °C 6: 218 mg / aq. NaOH / dioxane; methanol / 2 h / 20 °C 7: 96 percent / H2 / Pd/C / methanol; dioxane / 20 °C 8: 85 percent / K2CO3 / acetone / 0.5 h / Heating 9: 91 percent / K2CO3 / acetone / 0.33 h / Heating 10: TsOH*H2O; AcOH / toluene / 0.75 h / 110 °C 11: 95 percent / BCl3 / CH2Cl2 / 0.25 h / 15 °C 12: 66 percent / aq. NaOH / methanol; dioxane / 1 h / 20 °C View Scheme

1: 82 percent / potassium carbonate / dimethylformamide / 1 h / 70 °C 2: potassium hydroxide / ethanol / 1 h / Heating 3: 5.48 g / aq. HCl / ethanol; CHCl3 / 1 h / 40 °C 4: 88 percent / potassium carbonate / dimethylformamide / 0.5 h / 60 - 70 °C 5: [hydroxy(tosyloxy)iodo]benzene / CHCl3 / 24 h / 20 °C 6: 3.82 g / aq. sodium hydroxide; methanol / CHCl3 / 5 h / 25 °C 7: 91 percent / triethylamine; PPh3; CuI / PdCl2 / dimethylformamide / 2 h / 80 °C 8: 88 percent / hydrogen / palladium on carbon / methanol; dioxane 9: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C 10: 84 percent / potassium carbonate / acetone / 2 h / Heating 11: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 12: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 13: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme