sodium hydroxide in 1,4-dioxane; methanol T=20°C; 14 h;

N-ethyl-N,N-diisopropylamine in methanol; dichloromethane; chloroform; benzene

1: 1.) AlCl3 / 1.) CH2Cl2, 20 deg C, 1 h, 2.) CH2Cl2, 25 deg C, 1 h 2: 90 percent / K2CO3 / dimethylformamide / 3 h / 40 °C 3: 86.3 percent / H2 / 10 percent Pd/C / ethanol; dioxane / 0.75 h / 20 °C / 2280 Torr 4: 77.2 percent / iPr2EtN / CH2Cl2 / Ambient temperature 5: 87.5 percent / 1 N aq. NaOH / dioxane; methanol / 14 h / 20 °C View Scheme

1: 1.) AlCl3 / 1.) CH2Cl2, 20 deg C, 1 h, 2.) CH2Cl2, 25 deg C, 1 h 2: 90 percent / K2CO3 / dimethylformamide / 3 h / 40 °C 3: 86.3 percent / H2 / 10 percent Pd/C / ethanol; dioxane / 0.75 h / 20 °C / 2280 Torr 4: 77.2 percent / iPr2EtN / CH2Cl2 / Ambient temperature 5: 87.5 percent / 1 N aq. NaOH / dioxane; methanol / 14 h / 20 °C View Scheme

1: 90 percent / K2CO3 / dimethylformamide / 3 h / 40 °C 2: 86.3 percent / H2 / 10 percent Pd/C / ethanol; dioxane / 0.75 h / 20 °C / 2280 Torr 3: 77.2 percent / iPr2EtN / CH2Cl2 / Ambient temperature 4: 87.5 percent / 1 N aq. NaOH / dioxane; methanol / 14 h / 20 °C View Scheme