Multi-step reaction with 9 steps
1: bromine; zinc(II) chloride / chloroform / 25 - 65 °C / Inert atmosphere
2: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene / 25 - 100 °C / Inert atmosphere
3: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chlorobenzene / 25 - 85 °C
4: N,N-dimethyl-formamide / ethyl acetate / 4 h / 25 °C / Inert atmosphere
5: benzene; tetrahydrofuran / 0 - 25 °C
6: sodium hydroxide; water / ethanol / 25 - 75 °C
7: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 0 - 25 °C / Inert atmosphere
8: triethylamine / dichloromethane / 0 - 25 °C
9: tetrahydrofuran / 25 - 75 °C
With
N-Bromosuccinimide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); water; bromine; potassium carbonate; triethylamine; N,N-dimethyl-formamide; sodium hydroxide; zinc(II) chloride;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; ethanol; dichloromethane; chloroform; ethyl acetate; chlorobenzene; toluene; benzene;
2: Suzuki Coupling;