Multi-step reaction with 12 steps
1.1: bromine; acetic acid / 4 h / 20 °C
2.1: triethylamine / dichloromethane / 0.33 h / -70 °C
3.1: lithium chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 3 h / 70 °C / Inert atmosphere
3.2: 0.17 h / 70 °C
4.1: methanesulfonamide; hydroquinine 1,4-phthalazinediyl diether / water; tert-butyl alcohol / 72 h / 0 °C
5.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
6.1: perchloric acid / 1.5 h / 0 - 20 °C
7.1: platinum on activated charcoal; hydrogen / ethanol / 3 h / 20 °C
8.1: acetic acid / 0.5 h / 20 °C
8.2: 2 h / 20 °C
9.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 3 h / 110 °C / Microwave irradiation
10.1: copper(ll) bromide; tert.-butylnitrite / acetonitrile; water / 1 h / 23 °C
11.1: tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 4.5 h / 90 °C / Microwave irradiation; Sealed tube; Inert atmosphere
12.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 1 h / 110 °C / Microwave irradiation; Sealed tube; Inert atmosphere
With
pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); tert.-butylnitrite; perchloric acid; methanesulfonamide; hydroquinine 1,4-phthalazinediyl diether; platinum on activated charcoal; hydrogen; bromine; potassium carbonate; acetic acid; triethylamine; lithium chloride; copper(ll) bromide;
In
1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;