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

1: 75 percent / 1.) NaH / dimethylformamide / 1.) 0 deg.C, 30 min, 2.) 30 deg.C, 3 h 2: 1.) Mg / 1.) THF, reflux, 2.5 h, 2.) THF, reflux 3 h 3: 82 percent / pyridinium chlorochromate / CH2Cl2 / 36 h / 25 °C 4: 90 percent / tetrahydrofuran / 1.) -78 deg. C, 1 h, 2.) -78 - 0 deg.C, 1 h 5: 100 percent / phosphoryl chloride / CH2Cl2 / 1 h / 25 °C 6: 91 percent / H2 / 10percent Pd/C / ethyl acetate / 48 h / 3102.9 Torr 7: 68 percent / DDQ / CH2Cl2 / 1 h View Scheme

1: 1.) AlCl3, Br2, 2.) NaBH4 / 1.) CH2Cl2, 40 deg.C, 30 min, 2.) CH3OH, 0 deg.C, 2 h 2: 75 percent / 1.) NaH / dimethylformamide / 1.) 0 deg.C, 30 min, 2.) 30 deg.C, 3 h 3: 1.) Mg / 1.) THF, reflux, 2.5 h, 2.) THF, reflux 3 h 4: 82 percent / pyridinium chlorochromate / CH2Cl2 / 36 h / 25 °C 5: 90 percent / tetrahydrofuran / 1.) -78 deg. C, 1 h, 2.) -78 - 0 deg.C, 1 h 6: 100 percent / phosphoryl chloride / CH2Cl2 / 1 h / 25 °C 7: 91 percent / H2 / 10percent Pd/C / ethyl acetate / 48 h / 3102.9 Torr 8: 68 percent / DDQ / CH2Cl2 / 1 h View Scheme

1: 1.) Mg / 1.) THF, reflux, 2.5 h, 2.) THF, reflux 3 h 2: 82 percent / pyridinium chlorochromate / CH2Cl2 / 36 h / 25 °C 3: 90 percent / tetrahydrofuran / 1.) -78 deg. C, 1 h, 2.) -78 - 0 deg.C, 1 h 4: 100 percent / phosphoryl chloride / CH2Cl2 / 1 h / 25 °C 5: 91 percent / H2 / 10percent Pd/C / ethyl acetate / 48 h / 3102.9 Torr 6: 68 percent / DDQ / CH2Cl2 / 1 h View Scheme

1: 91 percent / H2 / 10percent Pd/C / ethyl acetate / 48 h / 3102.9 Torr 2: 68 percent / DDQ / CH2Cl2 / 1 h View Scheme

1: 90 percent / tetrahydrofuran / 1.) -78 deg. C, 1 h, 2.) -78 - 0 deg.C, 1 h 2: 100 percent / phosphoryl chloride / CH2Cl2 / 1 h / 25 °C 3: 91 percent / H2 / 10percent Pd/C / ethyl acetate / 48 h / 3102.9 Torr 4: 68 percent / DDQ / CH2Cl2 / 1 h View Scheme

1: 100 percent / phosphoryl chloride / CH2Cl2 / 1 h / 25 °C 2: 91 percent / H2 / 10percent Pd/C / ethyl acetate / 48 h / 3102.9 Torr 3: 68 percent / DDQ / CH2Cl2 / 1 h View Scheme

1: 82 percent / pyridinium chlorochromate / CH2Cl2 / 36 h / 25 °C 2: 90 percent / tetrahydrofuran / 1.) -78 deg. C, 1 h, 2.) -78 - 0 deg.C, 1 h 3: 100 percent / phosphoryl chloride / CH2Cl2 / 1 h / 25 °C 4: 91 percent / H2 / 10percent Pd/C / ethyl acetate / 48 h / 3102.9 Torr 5: 68 percent / DDQ / CH2Cl2 / 1 h View Scheme