3-chloro-benzenecarboperoxoic acid in dichloromethane T=4°C; 360 h; phosphate buffer (pH 8);

1: H2 / 10percent Pd on charcoal / ethyl acetate / 72 h / 2844.3 Torr 2: 98 percent / 1.) AlCl3, 2.) ice / CH2Cl2 / 1.) 0 deg C then RT 2 h 3: 98 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 72 h / Heating 4: 98 percent / NaBH4 / methanol / 2 h 5: 79 percent / p-toluenesulfonic acid / benzene / 20 h / Heating 6: 73 percent / m-chloroperbenzoic acid / CH2Cl2 / 360 h / 4 °C / phosphate buffer (pH 8) View Scheme

1: 98 percent / 1.) AlCl3, 2.) ice / CH2Cl2 / 1.) 0 deg C then RT 2 h 2: 98 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 72 h / Heating 3: 98 percent / NaBH4 / methanol / 2 h 4: 79 percent / p-toluenesulfonic acid / benzene / 20 h / Heating 5: 73 percent / m-chloroperbenzoic acid / CH2Cl2 / 360 h / 4 °C / phosphate buffer (pH 8) View Scheme

1: 79 percent / p-toluenesulfonic acid / benzene / 20 h / Heating 2: 73 percent / m-chloroperbenzoic acid / CH2Cl2 / 360 h / 4 °C / phosphate buffer (pH 8) View Scheme

1: 98 percent / NaBH4 / methanol / 2 h 2: 79 percent / p-toluenesulfonic acid / benzene / 20 h / Heating 3: 73 percent / m-chloroperbenzoic acid / CH2Cl2 / 360 h / 4 °C / phosphate buffer (pH 8) View Scheme

1: 98 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 72 h / Heating 2: 98 percent / NaBH4 / methanol / 2 h 3: 79 percent / p-toluenesulfonic acid / benzene / 20 h / Heating 4: 73 percent / m-chloroperbenzoic acid / CH2Cl2 / 360 h / 4 °C / phosphate buffer (pH 8) View Scheme