2,3-dicyano-5,6-dichloro-p-benzoquinone in toluene T=110°C; 36 h;

1.1: 2,3-dichloro-5,6-dicyanobenzoquinone / toluene / 36 h / 110 °C 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -20 °C 2.2: chlorodimethylaluminum / hexane; tetrahydrofuran / 0.5 h / -20 °C 2.3: 92 percent / hexane; tetrahydrofuran / 1 h / -20 °C 3.1: 2,3-dichloro-5,6-dicyanobenzoquinone / toluene / 12 h / 110 °C 4.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -20 °C 4.2: chlorodimethylaluminum / hexane; tetrahydrofuran / 0.5 h / -20 °C 4.3: 93 percent / hexane; tetrahydrofuran / 1 h / -20 °C 5.1: 2,3-dichloro-5,6-dicyanobenzoquinone / toluene / 12 h / 110 °C 6.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -20 °C 6.2: chlorodimethylaluminum / hexane; tetrahydrofuran / 0.5 h / -20 °C 6.3: 89 percent / hexane; tetrahydrofuran / 1 h / -20 °C 7.1: 2,3-dichloro-5,6-dicyanobenzoquinone / toluene / 24 h / 110 °C 8.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -20 °C 8.2: chlorodimethylaluminum / hexane; tetrahydrofuran / 0.5 h / -20 °C 8.3: 97 percent / hexane; tetrahydrofuran / 1 h / -20 °C 9.1: 2,3-dichloro-5,6-dicyanobenzoquinone / toluene / 24 h / 110 °C 10.1: n-butyllithium / hexane; tetrahydrofuran / cooling 10.2: hexane; tetrahydrofuran / -20 °C 10.3: tetrahydrofuran; hexane; diethyl ether / -20 °C 11.1: trichloroacetic acid / CH2Cl2 / 0.75 h / 25 - 30 °C 12.1: trichloroacetic acid / CH2Cl2 / 0.5 h / 25 - 30 °C 13.1: n-butyllithium / hexane; tetrahydrofuran / -78 - 20 °C 13.2: 85 percent / tetrahydrofuran; hexane / 1 h / -20 °C 14.1: trichloroacetic acid / CH2Cl2 / 1.5 h / 28 °C View Scheme

2,3-dicyano-5,6-dichloro-p-benzoquinone in toluene T=110°C; 36 h;