2,3-dicyano-5,6-dichloro-p-benzoquinone in toluene 15 h; Heating;

1.1: 100 percent / H2 / Pd/C / ethyl acetate; methanol / 5 h / 2068.59 Torr 2.1: K2CO3 / acetone; acetonitrile / 15 h / Heating 3.1: 1.26 g / KOH / methanol; H2O / 10 h / 70 °C 4.1: oxalyl chloride / CH2Cl2 / 20 h / 20 °C 5.1: tetrahydrofuran; hexane; acetonitrile / 4 h 6.1: 183 mg / rhodium (II) acetate dimer / CH2Cl2 / 1 h / Heating 7.1: phosphorus tribromide / CHCl3 / 1 h / 0 °C 7.2: 20 percent / CHCl3 / 1 h / Heating 8.1: 84 percent / DDQ / toluene / 15 h / Heating View Scheme

1.1: K2CO3 / acetone; acetonitrile / 15 h / Heating 2.1: 1.26 g / KOH / methanol; H2O / 10 h / 70 °C 3.1: oxalyl chloride / CH2Cl2 / 20 h / 20 °C 4.1: tetrahydrofuran; hexane; acetonitrile / 4 h 5.1: 183 mg / rhodium (II) acetate dimer / CH2Cl2 / 1 h / Heating 6.1: phosphorus tribromide / CHCl3 / 1 h / 0 °C 6.2: 20 percent / CHCl3 / 1 h / Heating 7.1: 84 percent / DDQ / toluene / 15 h / Heating View Scheme

1.1: oxalyl chloride / CH2Cl2 / 20 h / 20 °C 2.1: tetrahydrofuran; hexane; acetonitrile / 4 h 3.1: 183 mg / rhodium (II) acetate dimer / CH2Cl2 / 1 h / Heating 4.1: phosphorus tribromide / CHCl3 / 1 h / 0 °C 4.2: 20 percent / CHCl3 / 1 h / Heating 5.1: 84 percent / DDQ / toluene / 15 h / Heating View Scheme

1.1: 1.26 g / KOH / methanol; H2O / 10 h / 70 °C 2.1: oxalyl chloride / CH2Cl2 / 20 h / 20 °C 3.1: tetrahydrofuran; hexane; acetonitrile / 4 h 4.1: 183 mg / rhodium (II) acetate dimer / CH2Cl2 / 1 h / Heating 5.1: phosphorus tribromide / CHCl3 / 1 h / 0 °C 5.2: 20 percent / CHCl3 / 1 h / Heating 6.1: 84 percent / DDQ / toluene / 15 h / Heating View Scheme

1.1: tetrahydrofuran; hexane; acetonitrile / 4 h 2.1: 183 mg / rhodium (II) acetate dimer / CH2Cl2 / 1 h / Heating 3.1: phosphorus tribromide / CHCl3 / 1 h / 0 °C 3.2: 20 percent / CHCl3 / 1 h / Heating 4.1: 84 percent / DDQ / toluene / 15 h / Heating View Scheme

1.1: 183 mg / rhodium (II) acetate dimer / CH2Cl2 / 1 h / Heating 2.1: phosphorus tribromide / CHCl3 / 1 h / 0 °C 2.2: 20 percent / CHCl3 / 1 h / Heating 3.1: 84 percent / DDQ / toluene / 15 h / Heating View Scheme

1.1: phosphorus tribromide / CHCl3 / 1 h / 0 °C 1.2: 20 percent / CHCl3 / 1 h / Heating 2.1: 84 percent / DDQ / toluene / 15 h / Heating View Scheme