hydrogen iodide; acetic acid T=140°C; 1.5 h; Inert atmosphere;

potassium carbonate in tetrahydrofuran; methanol T=0°C; 0.5 h;

1: 97 percent / pyridine, piperidine / 1.) from 80 deg C to 85 deg C, 30 min, 2.) reflux, 4 h 2: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 5 h / 1810.02 Torr 3: 99.7 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 4: 98.6 percent / Et3N / CH2Cl2 / 0.25 h / 0 - 5 °C 5: aq. tricaprylylmethylammonium chloride / benzene / 15 h / Heating 6: aq. KOH / ethane-1,2-diol / 8 h / Heating 7: 53 percent / polyphosphoric acid / 2 h / 100 - 105 °C 8: 48percent aq. HBr, CH3CO2H / 2 h / Heating 9: NaBH4 / ethanol / 0.5 h 10: p-toluenesulfonic acid / benzene / 1 h / Heating 11: pyridine / 3 h 12: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 13: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: p-toluenesulfonic acid / 15 h / Heating 2: 1.) Mg, ethylene dibromide, 2.) B2H6, 3.) aq. NaOH, H2O2 3: NaBH4 / ethanol / 0.5 h 4: p-toluenesulfonic acid / benzene / 1 h / Heating 5: pyridine / 3 h 6: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 7: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: NaBH4 / ethanol / 0.5 h 2: p-toluenesulfonic acid / benzene / 1 h / Heating 3: pyridine / 3 h 4: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 5: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 2: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: 1.) Mg, ethylene dibromide, 2.) B2H6, 3.) aq. NaOH, H2O2 2: NaBH4 / ethanol / 0.5 h 3: p-toluenesulfonic acid / benzene / 1 h / Heating 4: pyridine / 3 h 5: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 6: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: 1.) Br2, 2.) silver fluoride / 1.) CCl4, RT, 1 h, 2.) THF, H2O, 30 min 2: p-toluenesulfonic acid / 15 h / Heating 3: 1.) Mg, ethylene dibromide, 2.) B2H6, 3.) aq. NaOH, H2O2 4: NaBH4 / ethanol / 0.5 h 5: p-toluenesulfonic acid / benzene / 1 h / Heating 6: pyridine / 3 h 7: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 8: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: 98.6 percent / Et3N / CH2Cl2 / 0.25 h / 0 - 5 °C 2: aq. tricaprylylmethylammonium chloride / benzene / 15 h / Heating 3: aq. KOH / ethane-1,2-diol / 8 h / Heating 4: 53 percent / polyphosphoric acid / 2 h / 100 - 105 °C 5: 48percent aq. HBr, CH3CO2H / 2 h / Heating 6: NaBH4 / ethanol / 0.5 h 7: p-toluenesulfonic acid / benzene / 1 h / Heating 8: pyridine / 3 h 9: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 10: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: p-toluenesulfonic acid / benzene / 1 h / Heating 2: pyridine / 3 h 3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 4: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme