2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane; water T=0 - 25°C; Oxidation; 1 h;

1.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 0.33 h / 0 - 20 °C 1.2: hexane; tetrahydrofuran / 1 h / 20 °C 2.1: 482 mg / PPTS / ethanol / 20 h / 20 °C View Scheme

1.1: oxalyl chloride; Et3N; DMSO / CH2Cl2 / 0.33 h / -78 - 0 °C 2.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 0.33 h / 0 - 20 °C 2.2: hexane; tetrahydrofuran / 1 h / 20 °C 3.1: 482 mg / PPTS / ethanol / 20 h / 20 °C View Scheme

1.1: NaH / tetrahydrofuran / 1 h / 0 °C 1.2: 95 percent / tetrabutylammonium iodide / tetrahydrofuran / 14 h / 25 °C 2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 2.2: tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 15 h / 0 - 25 °C 3.1: 3.03 g / HCl; water / tetrahydrofuran / 1.5 h / 0 - 25 °C 4.1: 97 percent / hydrogen; quinoline / Pd/CaCO3 / methanol / 4 h / 25 °C 5.1: 100 percent / imidazole / dimethylformamide / 18 h / 0 - 25 °C 6.1: 88 percent / dichlorodicyanobenzoquinone / CH2Cl2; H2O / 1 h / 0 - 25 °C View Scheme

1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 1.2: tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 15 h / 0 - 25 °C 2.1: 3.03 g / HCl; water / tetrahydrofuran / 1.5 h / 0 - 25 °C 3.1: 97 percent / hydrogen; quinoline / Pd/CaCO3 / methanol / 4 h / 25 °C 4.1: 100 percent / imidazole / dimethylformamide / 18 h / 0 - 25 °C 5.1: 88 percent / dichlorodicyanobenzoquinone / CH2Cl2; H2O / 1 h / 0 - 25 °C View Scheme

1: 97 percent / hydrogen; quinoline / Pd/CaCO3 / methanol / 4 h / 25 °C 2: 100 percent / imidazole / dimethylformamide / 18 h / 0 - 25 °C 3: 88 percent / dichlorodicyanobenzoquinone / CH2Cl2; H2O / 1 h / 0 - 25 °C View Scheme

1: 100 percent / imidazole / dimethylformamide / 18 h / 0 - 25 °C 2: 88 percent / dichlorodicyanobenzoquinone / CH2Cl2; H2O / 1 h / 0 - 25 °C View Scheme

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=20°C; 8 h;