Multi-step reaction with 8 steps
1.1: sulfuric acid; N-Bromosuccinimide / 2 h / 20 °C
2.1: iron; ammonium chloride / ethanol / 3 h / Reflux
3.1: dmap; triethylamine / N,N-dimethyl-formamide
4.1: sec.-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran / 2 h / -65 °C
4.2: 0.5 h / -65 - -10 °C
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 80 °C / Inert atmosphere
6.1: dihydrogen peroxide; water; sodium hydroxide / tetrahydrofuran / 0 - 10 °C
7.1: hydrogenchloride / 1,4-dioxane / 1 h / 0 - 20 °C
8.1: sodium hydrogencarbonate / tetrahydrofuran / 0.5 h / 0 - 20 °C
With
2,2,6,6-tetramethyl-piperidine; hydrogenchloride; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; sulfuric acid; water; dihydrogen peroxide; sec.-butyllithium; potassium acetate; iron; sodium hydrogencarbonate; ammonium chloride; triethylamine; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide;