2,3-dicyano-5,6-dichloro-p-benzoquinone in toluene 1 h; Heating;

sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride 3 h; Heating;

1: 97 percent / K2CO3, KI / acetone / 72 h / Heating 2: 48 percent / conc. aq. HCl, Fe powder / methanol / 0.5 h 3: 60 percent / various solvent(s) / 10 h / Heating 4: 72 percent / AcOK, cupric acetate monohydrate, triethylamine / propan-2-ol / 24 h / Heating 5: 85 percent / trifluoroacetic anhydride / CH2Cl2 / 72 h / 20 °C 6: 83 percent / benzyltriethylammonium chloride, 6N aq. NaOH / 3 h / Heating View Scheme

1: 72 percent / AcOK, cupric acetate monohydrate, triethylamine / propan-2-ol / 24 h / Heating 2: 85 percent / trifluoroacetic anhydride / CH2Cl2 / 72 h / 20 °C 3: 83 percent / benzyltriethylammonium chloride, 6N aq. NaOH / 3 h / Heating View Scheme

1: 60 percent / various solvent(s) / 10 h / Heating 2: 72 percent / AcOK, cupric acetate monohydrate, triethylamine / propan-2-ol / 24 h / Heating 3: 85 percent / trifluoroacetic anhydride / CH2Cl2 / 72 h / 20 °C 4: 83 percent / benzyltriethylammonium chloride, 6N aq. NaOH / 3 h / Heating View Scheme

1: 85 percent / trifluoroacetic anhydride / CH2Cl2 / 72 h / 20 °C 2: 83 percent / benzyltriethylammonium chloride, 6N aq. NaOH / 3 h / Heating View Scheme

1: 48 percent / conc. aq. HCl, Fe powder / methanol / 0.5 h 2: 60 percent / various solvent(s) / 10 h / Heating 3: 72 percent / AcOK, cupric acetate monohydrate, triethylamine / propan-2-ol / 24 h / Heating 4: 85 percent / trifluoroacetic anhydride / CH2Cl2 / 72 h / 20 °C 5: 83 percent / benzyltriethylammonium chloride, 6N aq. NaOH / 3 h / Heating View Scheme