Multi-step reaction with 11 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 80 °C
1.2: 20 °C
2.1: hydrogenchloride; water / Reflux
3.1: iron; acetic acid / 0.5 h / 20 °C
4.1: potassium acetate / toluene / 2 h / 60 °C
4.2: 8 h / 85 °C / Inert atmosphere
5.1: methanol; potassium carbonate / 2 h / Reflux
6.1: ethanol / 2 h / Reflux
7.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 8 h / 155 °C / Inert atmosphere
8.1: potassium tert-butylate; oxygen; dimethyl sulfoxide / tetrahydrofuran / 0.17 h / 20 °C
9.1: N-Bromosuccinimide / acetonitrile / 0.5 h / Reflux
10.1: potassium carbonate / ethanol / 2 h / Reflux
11.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 8 h / 155 °C / Inert atmosphere
With
hydrogenchloride; methanol; N-Bromosuccinimide; potassium tert-butylate; water; oxygen; potassium acetate; iron; sodium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene; acetonitrile;