Multi-step reaction with 9 steps
1.1: bromine / acetic acid / 2 h / 120 °C
2.1: diammonium sulfide / ethanol / 2 h / 90 °C
3.1: ethanol; water / 3 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C
5.1: caesium carbonate / bis(dibenzylideneacetone)-palladium(0); XPhos / 1,4-dioxane / 4 h / 82 °C / Inert atmosphere
6.1: hydrogen / palladium on activated charcoal / ethanol / 50 h / 60 °C / 3040.2 Torr
7.1: water; sodium nitrite; hydrogen bromide / 0.08 h / 0 - 5 °C
7.2: 0.5 h / 60 - 80 °C
8.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C
8.2: 3 h / 80 °C
9.1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane; water / 1 h / 100 °C / microwave irradiation
With
diammonium sulfide; water; hydrogen bromide; hydrogen; bromine; sodium carbonate; potassium carbonate; caesium carbonate; sodium nitrite;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium on activated charcoal; bis(dibenzylideneacetone)-palladium(0); XPhos;
In
1,4-dioxane; 1,2-dimethoxyethane; ethanol; water; acetic acid; N,N-dimethyl-formamide;