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

1: 91 percent / NaHCO3 / dimethylformamide / 12 h / 60 °C 2: 52 percent / diphenyl ether / 1 h / 225 - 230 °C 3: 72 percent / 85percent m-chloroperoxybenzoic acid / CH2Cl2 / 20 h / Ambient temperature 4: 41 percent / Jones reagent / acetone / 2 h 5: 95 percent / conc. H2SO4 / 1,2-dichloro-ethane / 1.5 h / Heating 6: dimethylformamide / 9 h / 160 - 163 °C 7: Fe powder / ethanol; acetic acid / 0.5 h / 80 - 85 °C 8: 68 percent / Cu2Br2, Na2CO3 / various solvent(s) / 5.5 h / 170 °C 9: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 6 h / Heating View Scheme

1: 87 percent / K2CO3 / dimethylformamide / 6 h / 60 °C 2: 47 percent / diphenyl ether / 1 h / 225 - 230 °C 3: 64 percent / 85percent m-chloroperoxybenzoic acid / CH2Cl2 / 20 h / Ambient temperature 4: 1) NaOH; 2) CH3COONa / 1) methanol, water, THF, 10 deg C, 1 h; 2) 140 deg C, 30 min. 5: 90 percent / conc. H2SO4 / methanol / 24 h / Ambient temperature 6: Jones reagent / acetone / 4 h 7: conc. H2SO4 / Ambient temperature; overnight 8: 65 percent / Fe powder / ethanol; acetic acid / 0.42 h 9: 68 percent / Cu2Br2, Na2CO3 / various solvent(s) / 5.5 h / 170 °C 10: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 6 h / Heating View Scheme

1: 72 percent / 85percent m-chloroperoxybenzoic acid / CH2Cl2 / 20 h / Ambient temperature 2: 41 percent / Jones reagent / acetone / 2 h 3: 95 percent / conc. H2SO4 / 1,2-dichloro-ethane / 1.5 h / Heating 4: dimethylformamide / 9 h / 160 - 163 °C 5: Fe powder / ethanol; acetic acid / 0.5 h / 80 - 85 °C 6: 68 percent / Cu2Br2, Na2CO3 / various solvent(s) / 5.5 h / 170 °C 7: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 6 h / Heating View Scheme

1: 52 percent / diphenyl ether / 1 h / 225 - 230 °C 2: 72 percent / 85percent m-chloroperoxybenzoic acid / CH2Cl2 / 20 h / Ambient temperature 3: 41 percent / Jones reagent / acetone / 2 h 4: 95 percent / conc. H2SO4 / 1,2-dichloro-ethane / 1.5 h / Heating 5: dimethylformamide / 9 h / 160 - 163 °C 6: Fe powder / ethanol; acetic acid / 0.5 h / 80 - 85 °C 7: 68 percent / Cu2Br2, Na2CO3 / various solvent(s) / 5.5 h / 170 °C 8: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 6 h / Heating View Scheme

1: 47 percent / diphenyl ether / 1 h / 225 - 230 °C 2: 64 percent / 85percent m-chloroperoxybenzoic acid / CH2Cl2 / 20 h / Ambient temperature 3: 1) NaOH; 2) CH3COONa / 1) methanol, water, THF, 10 deg C, 1 h; 2) 140 deg C, 30 min. 4: 90 percent / conc. H2SO4 / methanol / 24 h / Ambient temperature 5: Jones reagent / acetone / 4 h 6: conc. H2SO4 / Ambient temperature; overnight 7: 65 percent / Fe powder / ethanol; acetic acid / 0.42 h 8: 68 percent / Cu2Br2, Na2CO3 / various solvent(s) / 5.5 h / 170 °C 9: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 6 h / Heating View Scheme

1: 64 percent / 85percent m-chloroperoxybenzoic acid / CH2Cl2 / 20 h / Ambient temperature 2: 1) NaOH; 2) CH3COONa / 1) methanol, water, THF, 10 deg C, 1 h; 2) 140 deg C, 30 min. 3: 90 percent / conc. H2SO4 / methanol / 24 h / Ambient temperature 4: Jones reagent / acetone / 4 h 5: conc. H2SO4 / Ambient temperature; overnight 6: 65 percent / Fe powder / ethanol; acetic acid / 0.42 h 7: 68 percent / Cu2Br2, Na2CO3 / various solvent(s) / 5.5 h / 170 °C 8: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 6 h / Heating View Scheme

1: 1) NaOH; 2) CH3COONa / 1) methanol, water, THF, 10 deg C, 1 h; 2) 140 deg C, 30 min. 2: 90 percent / conc. H2SO4 / methanol / 24 h / Ambient temperature 3: Jones reagent / acetone / 4 h 4: conc. H2SO4 / Ambient temperature; overnight 5: 65 percent / Fe powder / ethanol; acetic acid / 0.42 h 6: 68 percent / Cu2Br2, Na2CO3 / various solvent(s) / 5.5 h / 170 °C 7: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 6 h / Heating View Scheme

1: 41 percent / Jones reagent / acetone / 2 h 2: 95 percent / conc. H2SO4 / 1,2-dichloro-ethane / 1.5 h / Heating 3: dimethylformamide / 9 h / 160 - 163 °C 4: Fe powder / ethanol; acetic acid / 0.5 h / 80 - 85 °C 5: 68 percent / Cu2Br2, Na2CO3 / various solvent(s) / 5.5 h / 170 °C 6: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 6 h / Heating View Scheme

1: 68 percent / Cu2Br2, Na2CO3 / various solvent(s) / 5.5 h / 170 °C 2: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 6 h / Heating View Scheme