1: 81 percent / Br2 / acetic acid / 1.) 45 deg C, 2.5 h, 2.) reflux, 4.75 h 2: 56 percent / ZnCl2 / benzene / 32 h / Heating 3: 86 percent / SnCl2*2H2O / ethanol / 1.) reflux, 0.5 h, 2.) room temp., 13 h 4: 1.) NaNO2, 48percent HBF4, 2.) 50percent aq. H3PO2 / 1.) H2O, 0 deg C, 2.5 h, 2.) CHCl3, 24 h, room temp. 5: 69 percent / conc. HCl / ethanol / 75 h / Heating 6: 1.) conc. HCl, NaNO2, 2.) KI / 1.) H2O, 0-5 deg C, 2.) room temp., 22 h 7: 58 percent / powdered Mg / tetrahydrofuran / 1 h / Heating 8: 1.) diborane, 2.) 3 N aq. NaOH, 30percent H2O2 / 1.) THF, 0 deg C, then 16 h room temp., 2.) 4 h, room temp. 9: 92 percent / benzoquinone, (t-BuO)3Al / benzene / 40 h / Heating View Scheme

1: 81 percent / Br2 / acetic acid / 1.) 45 deg C, 2.5 h, 2.) reflux, 4.75 h 2: 56 percent / ZnCl2 / benzene / 32 h / Heating 3: 86 percent / SnCl2*2H2O / ethanol / 1.) reflux, 0.5 h, 2.) room temp., 13 h 4: 1.) NaNO2, 48percent HBF4, 2.) 50percent aq. H3PO2 / 1.) H2O, 0 deg C, 2.5 h, 2.) CHCl3, 24 h, room temp. 5: 69 percent / conc. HCl / ethanol / 75 h / Heating 6: 1.) conc. HCl, NaNO2, 2.) KI / 1.) H2O, 0-5 deg C, 2.) room temp., 22 h 7: 58 percent / powdered Mg / tetrahydrofuran / 1 h / Heating 8: 1.) diborane, 2.) 3 N aq. NaOH, 30percent H2O2 / 1.) THF, 0 deg C, then 16 h room temp., 2.) 4 h, room temp. 9: 56 percent / benzoquinone, (t-BuO)3Al / benzene / 40 h / Heating View Scheme

sodium hydride in tetrahydrofuran T=0 - 20°C;

1: 81 percent / Br2 / acetic acid / 1.) 45 deg C, 2.5 h, 2.) reflux, 4.75 h 2: 56 percent / ZnCl2 / benzene / 32 h / Heating 3: 86 percent / SnCl2*2H2O / ethanol / 1.) reflux, 0.5 h, 2.) room temp., 13 h 4: 1.) NaNO2, 48percent HBF4, 2.) 50percent aq. H3PO2 / 1.) H2O, 0 deg C, 2.5 h, 2.) CHCl3, 24 h, room temp. 5: 69 percent / conc. HCl / ethanol / 75 h / Heating View Scheme

1: acetic acid; sulfuric acid; aqueous sodium nitrite solution; aqueous potassium iodide solution 2: copper-powder / 300 °C View Scheme

sodium iodide; sodium nitrite in sulfuric acid; water