diethyl ether; bromine Erwaermen des Reaktionsprodukts unter vermindertem Druck;

bromine; sodium hydrogencarbonate 1.) CCl4, O deg C; 2.) 25 deg C, 6 h; Yield given. Multistep reaction;

1: 98 percent / benzene / 1 h / Heating 2: acetic acid; methanol / 2 h / 200 °C 3: magnesium sulfate / CH2Cl2 / 0.02 h / 20 °C 4: 63 percent / benzene / 0.17 h / Heating 5: 66 percent / bis(benzonitrile)palladium(II) chloride, air / 2-methyl-propan-2-ol / 116 °C 6: 100 percent / aluminum isopropoxide / propan-2-ol / Heating 7: pyridine / 15 h / 20 °C 8: tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h / 100 °C 9: trifluoroacetic acid / CH2Cl2 / 0.5 h 10: 99 percent / N-methylmorpholine, osmium tetraoxide / tetrahydrofuran; H2O / 24 h / 20 °C 11: 1.) methyl sulfide, N-chlorosuccinimide, 2.) triethylamine / 1.) dichloromethane, -40 deg C, 1 h, 2.) from -40 to 20 deg C, 1.5 h 12: 97 percent / trifluoromethanesulfonic acid / CH2Cl2 / 24 h 13: 88 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Heating View Scheme