hydrogen bromide; acetic acid 5 h; Heating;

1: m-chloroperbenzoic acid 2: m-chloroperbenzoic acid 3: 60 percent / 48percent HBr / 120 °C View Scheme

1: 64 percent / (CH3CO)2O, 30percent H2O2 / 12 h / 80 °C 2: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 3: 1.) Na, 2.) PCl3 / 1.) MeOH, 24 h, room temp. 2.) chloroform, 2 h, reflux 4: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 5: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 6: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme

1: 44 percent / conc. H2SO4/H2SO4 (20percent SO3) (1:1); H2SO4 (20percent SO3)/100percent HNO3 / 1 h / Heating 2: 1.) Na, 2.) PCl3 / 1.) MeOH, 24 h, room temp. 2.) chloroform, 2 h, reflux 3: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 4: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 5: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme

1: 1.) Na, 2.) PCl3 / 1.) MeOH, 24 h, room temp. 2.) chloroform, 2 h, reflux 2: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 3: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 4: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme

1: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 2: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 3: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme

1: 80 percent / PCl3 / CHCl3 / 2 h / Heating 2: 52 percent / NiCl2*6H2O/(C6H5)3P, Zn, KI / dimethylformamide / 12 h / 50 °C 3: 53 percent / 30percent H2O2, (CH3CO)2O, / 14 h / 100 °C 4: 77 percent / 33percent HBr/CH3COOH / 5 h / Heating View Scheme

1: 35 percent / Br2, 10percent aq. NaOH / 24 h 2: 1.) NaOCH3 / 1.) MeOH, DMF; 2.) DMF, RT, 1.5 h 3: 90 percent / m-chloroperbenzoic acid / CHCl3 / 2.5 h / Ambient temperature 4: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C 5: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature 6: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 7: 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 8: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 9: 60 percent / 48percent aq. HBr / 5 h / 120 °C View Scheme

1: 1.) Br2; 2.) NaOCH3 / 1.) 10percent aq. NaOH, 24 h; 2.) MeOH, DMF, RT, 1.5 h 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: 1.) NaOCH3 / 1.) MeOH, DMF; 2.) DMF, RT, 1.5 h 2: 90 percent / m-chloroperbenzoic acid / CHCl3 / 2.5 h / Ambient temperature 3: 48 percent / fuming HNO3, conc. H2SO4 / 1 h / 60 °C 4: 78 percent / NaOCH3 / methanol / 2 h / Ambient temperature 5: 85 percent / PBr3 / CHCl3 / 0.5 h / 60 °C 6: 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 7: 85 percent / m-chloroperbenzoic acid / CHCl3 / 8 h / Ambient temperature 8: 60 percent / 48percent aq. HBr / 5 h / 120 °C View Scheme