N-bromosuccinmide in N,N-dimethyl-formamide T=70 - 80°C; 12 h;

1: With magnesium in tetrahydrofuran Grignard Reaction; Inert atmosphereReflux; 2: With dilithium tetrachlorocuprate(II); oxygen in tetrahydrofuran T=20°C; 2 h;

[2,2']bipyridinyl; nickel dichloride; zinc in N,N-dimethyl-formamide T=70°C; Dimerization; dehalogenation; 3 h;

lead(IV) acetate; boron trifluoride diethyl etherate in acetonitrile 3 h; Ambient temperature;

quinoline; copper Heating;

1: 62 percent / N-bromosuccinimide / dimethylformamide / 12 h / 70 - 80 °C 2: 1) n-BuLi / 2) CoCl2 / 1) ether, hexane, -10 to 0 deg C, 2 h, 2) reflux, 12 h 3: 60 percent / 2,3-dichloro-5,6-dicyanoquinone (DDQ) / benzene / 3 h / Heating View Scheme

sulfuric acid; nitric acid; acetic acid