bromine; sodium acetate in acetic acid T=80°C; 3 h;

1: Br2 / acetic acid / Ambient temperature 2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) -78 deg C View Scheme

n-butyllithium 1.) THF, hexane, -78 deg C, 2.) -78 deg C; Multistep reaction;

thionyl chloride; N,N-dimethyl-formamide in chloroform 2 h; Heating;

1: SOCl2, N,N-dimethylformamide / CHCl3 / 2 h / Heating 2: CHCl3 / 2 h / Ambient temperature 3: 1.) hexabutylditin, palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), triethylamine, 2.) I2 / 1.) 85 deg C, 2.5 h, 2.) CH3Cl, RT View Scheme