copper acetylacetonate; potassium phosphate; ammonia in N,N-dimethyl-formamide T=90°C; 24 h; GloveboxAutoclave; chemoselective reaction;

1: 90 percent / m-chloroperbenzoic acid / CHCl3 / 2.5 h / Ambient temperature 2: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C 3: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature 4: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 5: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 6: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 7: 60 percent / 48percent aq. HBr / 5 h / 120 °C View Scheme

1: 90 percent / m-chloroperbenzoic acid / CHCl3 / 2.5 h / Ambient temperature 2: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C 3: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature 4: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 5: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions View Scheme

1: 90 percent / m-chloroperbenzoic acid / CHCl3 / 2.5 h / Ambient temperature 2: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C 3: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature 4: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 5: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 6: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature View Scheme

1: 90 percent / m-chloroperbenzoic acid / CHCl3 / 2.5 h / Ambient temperature 2: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C 3: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature 4: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 5: 1.) NiCl2*6H2O, Ph3P, Zn powder / 1.) DMF, 50 deg C, 1 h; 2.) DMF, 50 deg C, 2 h; other cond.: Cu, KI, DMF or Pd/C, phase transfer conditions 6: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 7: 60 percent / 48percent aq. HBr / 5 h / 120 °C 8: 50 percent / 220 °C / 0.01 Torr / sublimation View Scheme

1: 71 percent / fuming HNO3, concd H2SO4 / 1 h / 55 °C 2: 59 percent / H2, NaOH / 10percent Pd/C / ethanol 3: 59 percent / xylene / 24 h / Heating 4: 30percent HBr, AcOH / 120 h / 100 °C View Scheme

hydrogenchloride; potassium hydroxide in sodium hydroxide; water; dimethyl sulfoxide

2-mercaptoethanesulphonic acid sodium salt in N,N-dimethyl-formamide T=60°C; 4 h;