sodium hydroxide in 1,4-dioxane; methanol T=20°C; 1 h;

1: 96 percent / H2 / Pd/C / methanol; dioxane / 20 °C 2: 85 percent / K2CO3 / acetone / 0.5 h / Heating 3: 91 percent / K2CO3 / acetone / 0.33 h / Heating 4: TsOH*H2O; AcOH / toluene / 0.75 h / 110 °C 5: 95 percent / BCl3 / CH2Cl2 / 0.25 h / 15 °C 6: 66 percent / aq. NaOH / methanol; dioxane / 1 h / 20 °C View Scheme

1: thallium(III) nitrate trihydrate / CHCl3 / 4 h / 40 °C 2: 995 mg / aq. NaOH / dioxane; methanol / 2 h / 20 °C 3: 96 percent / H2 / Pd/C / methanol; dioxane / 20 °C 4: 85 percent / K2CO3 / acetone / 0.5 h / Heating 5: 91 percent / K2CO3 / acetone / 0.33 h / Heating 6: TsOH*H2O; AcOH / toluene / 0.75 h / 110 °C 7: 95 percent / BCl3 / CH2Cl2 / 0.25 h / 15 °C 8: 66 percent / aq. NaOH / methanol; dioxane / 1 h / 20 °C View Scheme

1: 995 mg / aq. NaOH / dioxane; methanol / 2 h / 20 °C 2: 96 percent / H2 / Pd/C / methanol; dioxane / 20 °C 3: 85 percent / K2CO3 / acetone / 0.5 h / Heating 4: 91 percent / K2CO3 / acetone / 0.33 h / Heating 5: TsOH*H2O; AcOH / toluene / 0.75 h / 110 °C 6: 95 percent / BCl3 / CH2Cl2 / 0.25 h / 15 °C 7: 66 percent / aq. NaOH / methanol; dioxane / 1 h / 20 °C View Scheme

1: 92 percent / I2; aq. HIO4 / ethanol / 0.5 h / 40 °C 2: 80 percent / K2CO3 / dimethylformamide / 0.5 h / 70 °C 3: KOH / ethanol / 0.75 h / 80 °C 4: 2.35 g / aq. HCl / CHCl3; methanol / 1 h / 40 °C 5: 530 mg / pyridine / 0.5 h / 70 °C 6: thallium(III) nitrate trihydrate / CHCl3 / 4 h / 30 °C 7: 218 mg / aq. NaOH / dioxane; methanol / 2 h / 20 °C 8: 96 percent / H2 / Pd/C / methanol; dioxane / 20 °C 9: 85 percent / K2CO3 / acetone / 0.5 h / Heating 10: 91 percent / K2CO3 / acetone / 0.33 h / Heating 11: TsOH*H2O; AcOH / toluene / 0.75 h / 110 °C 12: 95 percent / BCl3 / CH2Cl2 / 0.25 h / 15 °C 13: 66 percent / aq. NaOH / methanol; dioxane / 1 h / 20 °C View Scheme

1: 94 percent / H2 / Pd/C / methanol; ethyl acetate / 18 - 23 °C 2: 92 percent / I2; aq. HIO4 / ethanol / 0.5 h / 40 °C 3: 80 percent / K2CO3 / dimethylformamide / 0.5 h / 70 °C 4: KOH / ethanol / 0.75 h / 80 °C 5: 2.35 g / aq. HCl / CHCl3; methanol / 1 h / 40 °C 6: 530 mg / pyridine / 0.5 h / 70 °C 7: thallium(III) nitrate trihydrate / CHCl3 / 4 h / 30 °C 8: 218 mg / aq. NaOH / dioxane; methanol / 2 h / 20 °C 9: 96 percent / H2 / Pd/C / methanol; dioxane / 20 °C 10: 85 percent / K2CO3 / acetone / 0.5 h / Heating 11: 91 percent / K2CO3 / acetone / 0.33 h / Heating 12: TsOH*H2O; AcOH / toluene / 0.75 h / 110 °C 13: 95 percent / BCl3 / CH2Cl2 / 0.25 h / 15 °C 14: 66 percent / aq. NaOH / methanol; dioxane / 1 h / 20 °C 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: KOH / ethanol / 0.75 h / 80 °C 2: 2.35 g / aq. HCl / CHCl3; methanol / 1 h / 40 °C 3: 530 mg / pyridine / 0.5 h / 70 °C 4: thallium(III) nitrate trihydrate / CHCl3 / 4 h / 30 °C 5: 218 mg / aq. NaOH / dioxane; methanol / 2 h / 20 °C 6: 96 percent / H2 / Pd/C / methanol; dioxane / 20 °C 7: 85 percent / K2CO3 / acetone / 0.5 h / Heating 8: 91 percent / K2CO3 / acetone / 0.33 h / Heating 9: TsOH*H2O; AcOH / toluene / 0.75 h / 110 °C 10: 95 percent / BCl3 / CH2Cl2 / 0.25 h / 15 °C 11: 66 percent / aq. NaOH / methanol; dioxane / 1 h / 20 °C View Scheme

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

1: thallium(III) nitrate trihydrate / CHCl3 / 4 h / 30 °C 2: 218 mg / aq. NaOH / dioxane; methanol / 2 h / 20 °C 3: 96 percent / H2 / Pd/C / methanol; dioxane / 20 °C 4: 85 percent / K2CO3 / acetone / 0.5 h / Heating 5: 91 percent / K2CO3 / acetone / 0.33 h / Heating 6: TsOH*H2O; AcOH / toluene / 0.75 h / 110 °C 7: 95 percent / BCl3 / CH2Cl2 / 0.25 h / 15 °C 8: 66 percent / aq. NaOH / methanol; dioxane / 1 h / 20 °C View Scheme