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

1: 91 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / benzene / 6 h / Heating 2: 54 percent / hydrogen, NaOAc*3H2O / Raney nickel / ethanol / 1 h / 2327.2 Torr / Ambient temperature View Scheme

bromine in acetic acid

1: concentrated sulfuric acid; nitric acid / 20 °C 2: aq.-ethanolic hydrochloric acid 3: acetic acid; bromine View Scheme

1: aq.-ethanolic hydrochloric acid 2: acetic acid; bromine View Scheme

1: acetyl chloride; acetic acid 2: platinum; ethanol / Hydrogenation View Scheme

1: 91 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / benzene / 6 h / Heating 2: 91 percent / acetic acid / 7 h / 70 °C 4: 92 percent / conc. HCl / 6 h / Heating View Scheme

1: 91 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / benzene / 6 h / Heating 2: 91 percent / acetic acid / 7 h / 70 °C 4: 92 percent / conc. HCl / 6 h / Heating 5: 100 percent / hydrogen, KOH / 10percent Pd on charcoal / H2O / 1.67 h / 2327.2 Torr / Ambient temperature View Scheme

1: 66 percent / pyridine / 13 h / 100 °C 2: 27 percent / K2CO3, benzyl triethylammonium chloride (BTAC) / dimethylsulfoxide / 155 °C 3: 93 percent / H2 / Pd/C / trifluoroacetic acid / 0.5 h / 25 °C / 760 Torr 4: 76 percent / ONOSO3H, NaBF4, H2SO4 / 1 h / 0 °C 5: 50 percent / H3PO2, Cu2O / 1,2-dichloro-ethane / 0.5 h / 70 °C View Scheme