n-butyllithium 1.) hexane, THF, 0 deg C, 30 min, 2.) hexane, THF, 2 h; Yield given. Multistep reaction. Yields of byproduct given;

3-chloro-benzenecarboperoxoic acid in dichloromethane T=0°C; 1 h;

1: 96 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / 0 °C 2: 1.) butyllithium / 1.) THF, hexane, 0 deg C; 2.) HMPA, reflux, 1 h 3: 1 M HCl / ethanol / 0.5 h / Ambient temperature 4: potassium hydride / tetrahydrofuran / 0.05 h / Ambient temperature View Scheme

1: 96 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / 0 °C 2: 1.) butyllithium / 1.) THF, hexane, 0 deg C; 2.) HMPA, reflux, 1 h 3: 1 M HCl / ethanol / 0.5 h / Ambient temperature View Scheme

1: 96 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / 0 °C 2: 1.) butyllithium / 1.) THF, hexane, 0 deg C; 2.) HMPA, reflux, 1 h 3: 1 M HCl / ethanol / 0.5 h / Ambient temperature 4: potassium hydride / tetrahydrofuran / 0.05 h / Ambient temperature View Scheme