sodium T=190°C; Heating / reflux;

acetic acid; zinc; sodium nitrite Reaktion ueber zwei Stufen;

sodium acetate; acetic acid; zinc

1: 90 percent / POCl3 / dimethylformamide / 0.75 h / 40 °C 2: 96 percent / KOH / H2O; dimethylformamide / 0.25 h / 20 °C 3: 99 percent / bromine / CCl4 / 1 h / 20 °C 4: 70 percent / aq. ethanol / 1 h / Heating 5: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere 6: 1.) 40percent HBr 2.) benzoyl chloride / 1.) glac.AcOH, 8 h, 20 degC 2.) DMF, 24 h, 20 degC 7: 90 percent / HBr / diethyl ether / 0.17 h 8: 88 percent / HBr / methanol / 0.17 h 9: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 10: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

hydrogen

1: sulfuryl dichloride; acetic acid / 20 °C / Inert atmosphere 2: tetrafluoroboric acid diethyl ether complex / 1,2-dichloro-ethane / 40 - 90 °C / Inert atmosphere 3: 10 palladium on activated carbon; hydrogen / tetrahydrofuran / 3 h / 20 °C / 750.08 Torr 4: iodine; sodium hydrogencarbonate / ethanol; water / 20 °C / Inert atmosphere 5: trifluorormethanesulfonic acid; acetic anhydride; acetic acid / 1 h / 20 °C / Inert atmosphere 6: sodium tetrahydroborate / methanol; dichloromethane / 1.33 h / 20 °C / Inert atmosphere View Scheme

methanol; nickel T=110 - 120°C; P=73550.8 Torr; Hydrogenation;

1.1: diborane 2.1: SO2Cl2 2.2: I2; KI 2.3: Zn; AcOH View Scheme

toluene-4-sulfonic acid; ethylene glycol 0.133333 h; microwave irradiation;