1: Br2 / acetic acid / Ambient temperature 2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) -78 deg C 3: SOCl2, N,N-dimethylformamide / CHCl3 / 2 h / Heating 4: CHCl3 / 2 h / Ambient temperature 5: 1.) hexabutylditin, palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), triethylamine, 2.) I2 / 1.) 85 deg C, 2.5 h, 2.) CH3Cl, RT View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) -78 deg C 2: SOCl2, N,N-dimethylformamide / CHCl3 / 2 h / Heating 3: CHCl3 / 2 h / Ambient temperature 4: 1.) hexabutylditin, palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), triethylamine, 2.) I2 / 1.) 85 deg C, 2.5 h, 2.) CH3Cl, RT View Scheme

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

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

tetrakis(triphenylphosphine) palladium(0); iodine; palladium diacetate; 1,1,1,2,2,2-hexabutyl-distannane; triethylamine 1.) 85 deg C, 2.5 h, 2.) CH3Cl, RT; Yield given. Multistep reaction;