hydrogenchloride; palladium on activated charcoal; hydrogen in acetic acid 120 h;

1: selenium(IV) oxide; dihydrogen peroxide / tert-butyl alcohol / 2.5 h / 50 °C 2: triethylamine / methanol / 0 - 20 °C 3: potassium carbonate / acetone / 36 h / 20 °C / Inert atmosphere 4: AlCl3, aluminium chloride / dichloromethane / 0 - 20 °C 5: lithium hexamethyldisilazane / tetrahydrofuran / -30 - 0 °C / Inert atmosphere 6: trifluoroacetic acid / methanol / 24 h / 50 °C View Scheme

potassium hydroxide; 3-chloro-benzenecarboperoxoic acid 1.) CH2Cl2, rt; 2.) MeOH; Yield given. Multistep reaction;

1: 67 percent / conc. HCl, H2, 10percent Pd-C / acetic acid / 120 h 2: 83 percent / Br2 / CH2Cl2 / 3 - 5 °C View Scheme

peracetic acid; perchloric acid; acetic anhydride in acetic acid

1: selenium(IV) oxide; dihydrogen peroxide / tert-butyl alcohol / 2.5 h / 50 °C 2: triethylamine / methanol / 0 - 20 °C 3: potassium carbonate / acetone / 36 h / 20 °C / Inert atmosphere 4: AlCl3, aluminium chloride / dichloromethane / 0 - 20 °C 5: lithium hexamethyldisilazane / tetrahydrofuran / -30 - 0 °C / Inert atmosphere 6: trifluoroacetic acid / methanol / 24 h / 50 °C 7: AlCl3, aluminium chloride; ethanethiol / CHCl2 / 0 - 20 °C View Scheme

urea hydrogen peroxide addition compound; sodium hydroxide in methanol; water 1.5 h; Reflux;

1: 67 percent / conc. HCl, H2, 10percent Pd-C / acetic acid / 120 h 2: 83 percent / Br2 / CH2Cl2 / 3 - 5 °C 4: PTA, CAN / acetonitrile; H2O / 0.33 h View Scheme