bis-triphenylphosphine-palladium(II) chloride; acetic anhydride; triethylamine in benzene T=160°C; P=45600 Torr; 1 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 4 h; Ambient temperature;

bis-triphenylphosphine-palladium(II) chloride; triethylamine in benzene T=160°C; P=45600 Torr; 1 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

boron trifluoride diethyl etherate T=0°C; 18 h;

1.1: NaH / tetrahydrofuran / 0.17 h / Heating 1.2: 88 percent / tetrahydrofuran / 6 h / Heating 2.1: 60 percent / acetic acid; chromic acid / H2O / 6 h / 20 °C 3.1: 60 percent / boron trifluoride etherate / 18 h / 0 °C View Scheme

1.1: NaBH4 / ethanol / 1 h / 0 °C 2.1: NaH / tetrahydrofuran / 0.17 h / Heating 2.2: 88 percent / tetrahydrofuran / 6 h / Heating 3.1: 60 percent / acetic acid; chromic acid / H2O / 6 h / 20 °C 4.1: 60 percent / boron trifluoride etherate / 18 h / 0 °C View Scheme

sodium hydroxide in ethanol