1: With hydrogenchloride; sodium nitrite in water T=-5 - 0°C; 0.333333 h; 2: With HPF6 in water 3: With sodium hydroxide more than 3 stages;

1: m-chloroperbenzoic acid / CH2Cl2 / 16 h / Ambient temperature 2: 72 percent / HNO3, 30percent oleum, conc. H2SO4 / 1) 5 deg C to RT, 1 h, 2) steam bath, 2 h 3: 89 percent / POCl3 / CH2Cl2 / 1) RT, 16 h, 2) reflux, 4 h 4: 53 percent / trifluoroacetic anhydride / CH2Cl2 / 168 h / Ambient temperature View Scheme

potassium permanganate in water

1: m-chloroperbenzoic acid / CH2Cl2 / 16 h / Ambient temperature 2: 72 percent / HNO3, 30percent oleum, conc. H2SO4 / 1) 5 deg C to RT, 1 h, 2) steam bath, 2 h View Scheme

3-chloro-benzenecarboperoxoic acid in dichloromethane 16 h; Ambient temperature; Yield given;