1: 92 percent / Br2; AcONa; Fe / acetic acid / 5 h 2: 66 percent / KOH / methanol / 16 h / Heating View Scheme

1: 27 percent / conc. HNO3 / 0.75 h 2: 88 percent / Fe(OH)2 / H2O / 20 h / Heating 3: 1.) 40 percent HBr, NaNO2; 2.) Cu / 1.) H2O; 2.) H2O 4: 23 percent / K2CO3 / acetone / 18 h / 60 - 70 °C View Scheme

1: 88 percent / Fe(OH)2 / H2O / 20 h / Heating 2: 1.) 40 percent HBr, NaNO2; 2.) Cu / 1.) H2O; 2.) H2O 3: 23 percent / K2CO3 / acetone / 18 h / 60 - 70 °C View Scheme

2: 27 percent / conc. HNO3 / 0.75 h 3: 88 percent / Fe(OH)2 / H2O / 20 h / Heating 4: 1.) 40 percent HBr, NaNO2; 2.) Cu / 1.) H2O; 2.) H2O 5: 23 percent / K2CO3 / acetone / 18 h / 60 - 70 °C View Scheme

potassium carbonate in N,N-dimethyl-formamide

1.1: 98 percent / NaBH4 / tetrahydrofuran; methanol / 2 h 2.1: SOCl2 / benzene / 20 °C 3.1: dimethylsulfoxide; benzene / 2 h 4.1: 92 percent / 4N NaOH / ethanol / 20 h / Heating 5.1: SOCl2 / benzene / 2 h / 50 - 60 °C 6.1: 91 percent / benzene; pyridine / 20 °C 7.1: 85 percent / POCl3 / toluene / 3 h / Heating 8.1: 92 percent / methylene blue; O2 / CH2Cl2; methanol / 0.5 h / 15 °C / Irradiation 9.1: 82 percent / acetonitrile / 1.25 h / Heating 10.1: 92 percent / H2 / PtO2 / methanol / 3 h / 17 °C 11.1: 90 percent / NaBH4 / methanol / 2 h 12.1: CuCl2 / toluene / 0.03 h / 140 °C 12.2: NaBH4 / methanol / 2 h / 20 °C View Scheme

1: 98 percent / NaBH4 / tetrahydrofuran; methanol / 2 h 2: SOCl2 / benzene / 20 °C 3: dimethylsulfoxide; benzene / 2 h 4: 92 percent / 4N NaOH / ethanol / 20 h / Heating 5: SOCl2 / benzene / 2 h / 50 - 60 °C 6: 91 percent / benzene; pyridine / 20 °C 7: 85 percent / POCl3 / toluene / 3 h / Heating 8: 92 percent / methylene blue; O2 / CH2Cl2; methanol / 0.5 h / 15 °C / Irradiation 9: 82 percent / acetonitrile / 1.25 h / Heating 10: 92 percent / H2 / PtO2 / methanol / 3 h / 17 °C 11: 81 percent / O2 / methanol / 1 h View Scheme

T=100°C;

sodium tetrahydroborate in tetrahydrofuran; methanol Reduction; 2 h;

T=100°C;