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

acetic acid

pyridinium chlorochromate in dichloromethane 12 h; Ambient temperature;

1: 93.2 percent / K2CO3, KI / dimethylformamide; benzene / 3 h / 85 °C 2: 91.7 percent / acetic acid / H2O / 0.5 h / Heating View Scheme

toluene-4-sulfonic acid in methanol 1 h; Ambient temperature;

1: 72 percent / DMAP, p-toluenesulfonyl chloride / CH2Cl2 / 3 h / Ambient temperature 2: 93.2 percent / K2CO3, KI / dimethylformamide; benzene / 3 h / 85 °C 3: 91.7 percent / acetic acid / H2O / 0.5 h / Heating View Scheme

1: 100 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C 2: 72 percent / DMAP, p-toluenesulfonyl chloride / CH2Cl2 / 3 h / Ambient temperature 3: 93.2 percent / K2CO3, KI / dimethylformamide; benzene / 3 h / 85 °C 4: 91.7 percent / acetic acid / H2O / 0.5 h / Heating View Scheme

1: 1) H2, quinoline, 2) Et3N, 4-dimethylaminopyridine / 1) Lindlar's catalyst / 1) methanol, 5 p.s.i., 2) CH2Cl2, RT, 2 h 2: 84 percent / phenylisocyanate, Et3N / benzene / Ambient temperature 3: 96 percent / Li2O*H2O / methanol; H2O / 0.17 h / 0 °C 4: 68 percent / diethyldiazocarboxylate, PPh3 / tetrahydrofuran / 24 h / Ambient temperature 5: 41 percent / Mo(CO)6 / acetonitrile; H2O / 2 h / Heating 6: 48 percent / p-TsOH / methanol; various solvent(s) / 1 h / Ambient temperature View Scheme

1: 93.2 percent / K2CO3, KI / dimethylformamide; benzene / 3 h / 85 °C 2: 91.7 percent / acetic acid / H2O / 0.5 h / Heating View Scheme

1: 20 percent / selenium dioxide, camphorsulfonic acid / dioxane / 1.5 h / 55 °C 2: 80 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 12 h / Ambient temperature View Scheme