3-chloro-benzenecarboperoxoic acid in dichloromethane T=0°C; 12 h;

1: 51.4 percent / NaBH4 / ethanol / 6 h 2: 94 percent / toluene-p-sulfonic acid / toluene / Heating 3: 91 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -40 deg C to room temperature, 2) room temperature, 12 h 4: 87 percent / N-bromosuccinimide, Me2S / CH2Cl2 / 5 h 5: 92 percent / m-chloroperbenzoic acid / CH2Cl2 / 12 h / 0 °C View Scheme

1: 94 percent / toluene-p-sulfonic acid / toluene / Heating 2: 91 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -40 deg C to room temperature, 2) room temperature, 12 h 3: 87 percent / N-bromosuccinimide, Me2S / CH2Cl2 / 5 h 4: 92 percent / m-chloroperbenzoic acid / CH2Cl2 / 12 h / 0 °C View Scheme

1: 91 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -40 deg C to room temperature, 2) room temperature, 12 h 2: 87 percent / N-bromosuccinimide, Me2S / CH2Cl2 / 5 h 3: 92 percent / m-chloroperbenzoic acid / CH2Cl2 / 12 h / 0 °C View Scheme

1: 87 percent / N-bromosuccinimide, Me2S / CH2Cl2 / 5 h 2: 92 percent / m-chloroperbenzoic acid / CH2Cl2 / 12 h / 0 °C View Scheme

1: 1) NaH / 1) toluene, reflux, 30 min, 2) reflux, 1 h 2: 51.4 percent / NaBH4 / ethanol / 6 h 3: 94 percent / toluene-p-sulfonic acid / toluene / Heating 4: 91 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -40 deg C to room temperature, 2) room temperature, 12 h 5: 87 percent / N-bromosuccinimide, Me2S / CH2Cl2 / 5 h 6: 92 percent / m-chloroperbenzoic acid / CH2Cl2 / 12 h / 0 °C View Scheme

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in diethyl ether