1: 35 percent / Fe(NO3)3*9H2O / ethanol / 16 h / Heating 2: 51 percent / MnO2 / toluene / 6 h / Heating View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 3 h / 0 °C 2.1: bromine; pyridine / dichloromethane / 2 h / 0 °C 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 3 h / 0 °C 2.1: bromine; pyridine / dichloromethane / 2 h / 0 °C 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C 5.1: copper(I) bromide; sodium / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux View Scheme

1: pyridine; benzene 2: aqueous peroxyacetic acid / Erhitzen des Reaktionsprodukts mit wss. NaOH View Scheme

iron nitrate (III) in ethanol 16 h; Heating;

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 3 h / 0 °C 2.1: bromine; pyridine / dichloromethane / 2 h / 0 °C 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 3 h / 0 °C 2.1: bromine; pyridine / dichloromethane / 2 h / 0 °C 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C 5.1: copper(I) bromide; sodium / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux 6.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C 6.2: 12.25 h / 0 - 25 °C View Scheme