3-chloro-benzenecarboperoxoic acid in dichloromethane T=0°C; 0.666667 h;

triethylamine T=0°C; 4.5 h;

1: 1.) DIBAH / 1.) toluene, 30 min, 2.) 20 min 2: 70 percent / HCl, CaCl2 / various solvent(s) / 0.17 h 3: 1.)NaH / 1.) dimethoxyethane, hexane, 0 deg C, 5 min, 2.) 35 min 4: 70 percent / Et3N / CH2Cl2 / 12 h / 20 °C 5: 27 percent / m-chloroperbenzoic acid / CH2Cl2 / 0.67 h / 0 °C View Scheme

1: 54 percent / Et3N / 1 h / Heating 2: 1.) DIBAH / 1.) toluene, 30 min, 2.) 20 min 3: 70 percent / HCl, CaCl2 / various solvent(s) / 0.17 h 4: 1.)NaH / 1.) dimethoxyethane, hexane, 0 deg C, 5 min, 2.) 35 min 5: 70 percent / Et3N / CH2Cl2 / 12 h / 20 °C 6: 27 percent / m-chloroperbenzoic acid / CH2Cl2 / 0.67 h / 0 °C View Scheme

1: 70 percent / HCl, CaCl2 / various solvent(s) / 0.17 h 2: 1.)NaH / 1.) dimethoxyethane, hexane, 0 deg C, 5 min, 2.) 35 min 3: 70 percent / Et3N / CH2Cl2 / 12 h / 20 °C 4: 27 percent / m-chloroperbenzoic acid / CH2Cl2 / 0.67 h / 0 °C View Scheme

1: 1.)NaH / 1.) dimethoxyethane, hexane, 0 deg C, 5 min, 2.) 35 min 2: 70 percent / Et3N / CH2Cl2 / 12 h / 20 °C 3: 27 percent / m-chloroperbenzoic acid / CH2Cl2 / 0.67 h / 0 °C View Scheme

1: 70 percent / Et3N / CH2Cl2 / 12 h / 20 °C 2: 27 percent / m-chloroperbenzoic acid / CH2Cl2 / 0.67 h / 0 °C View Scheme

1: 74 percent / BF3 / 1.) 0 deg C, 45 min, 2.) r.t., 30 min, 3.) 95 deg C, 12 h 2: 49 percent / triethylamine / 4.5 h / 0 °C View Scheme

1: 65 percent / acetic anhydride / 3 h / 95 °C 2: 74 percent / BF3 / 1.) 0 deg C, 45 min, 2.) r.t., 30 min, 3.) 95 deg C, 12 h 3: 49 percent / triethylamine / 4.5 h / 0 °C View Scheme

1: 74 percent / BF3 / 1.) 0 deg C, 45 min, 2.) r.t., 30 min, 3.) 95 deg C, 12 h 2: 49 percent / triethylamine / 4.5 h / 0 °C View Scheme