Multi-step reaction with 9 steps
1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C / Inert atmosphere
1.2: 0 °C / Inert atmosphere
2.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / Inert atmosphere; Reflux
3.1: boron tribromide / dichloromethane / 3.5 h / -30 - 20 °C / Inert atmosphere
4.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / Inert atmosphere; Reflux
5.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / Inert atmosphere; Reflux
6.1: triethylamine / dichloromethane / 3.5 h / -78 - 20 °C / Inert atmosphere
7.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / Inert atmosphere; Reflux
8.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / Inert atmosphere; Reflux
9.1: hydrogen / palladium 10% on activated carbon / methanol / 4 h / 20 °C
With
hydrogenchloride; hydrogen; potassium acetate; boron tribromide; sodium carbonate; triethylamine; sodium nitrite;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;
2.1: Suzuki Coupling / 5.1: Suzuki Coupling / 8.1: Suzuki Coupling;