2,3-dicyano-5,6-dichloro-p-benzoquinone in toluene 24 h; Heating;

1: 91 percent / thionyl chloride / 0 - 20 °C 2: 89 percent / triethylamine; 4-(dimethylamino)pyridine / tetrahydrofuran / 20 - 40 °C 3: 85 percent / DDQ / toluene / 24 h / Heating View Scheme

1: 89 percent / triethylamine; 4-(dimethylamino)pyridine / tetrahydrofuran / 20 - 40 °C 2: 85 percent / DDQ / toluene / 24 h / Heating View Scheme

1: acetic acid; iron / ethanol / 0.08 h / 20 °C / |Reflux 2: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 0 °C 3: potassium carbonate; 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide / 1,4-dioxane / 6 h / |Schlenk technique; |Inert atmosphere; |Reflux View Scheme

1.1: bromo-dimethylsulfonium bromide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 1.2: -78 - 20 °C / |Inert atmosphere 2.1: acetic acid; iron / ethanol / 0.08 h / 20 °C / |Reflux 3.1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 0 °C 4.1: potassium carbonate; 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide / 1,4-dioxane / 6 h / |Schlenk technique; |Inert atmosphere; |Reflux View Scheme