Multi-step reaction with 10 steps
1.1: bromine / dichloromethane / 36 h / 0 - 20 °C / Inert atmosphere
2.1: triethylamine / palladium diacetate; 1,1'-bis(diphenylphosphino)ferrocene / ethanol / 70 °C / Inert atmosphere
3.1: bromine; pyridine / dichloromethane / 2 h / 0 - 20 °C
4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -65 - 0 °C / Inert atmosphere
4.2: 2 h / 20 °C
5.1: trifluoromethylsulfonic anhydride / 1,2-dichloro-ethane / 50 °C / Inert atmosphere
6.1: potassium hydroxide; water / 5 h / 20 °C / Industry scale
6.2: 7 °C
7.1: triphenylphosphine; palladium diacetate / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere; Industry scale
8.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C / Industry scale
9.1: hydrogen / 5%-palladium/activated carbon / methanol / 3 h / 45 °C / 3750.38 Torr / Industry scale
10.1: caesium carbonate / palladium diacetate; 4,5’-bis(diphenylphosphino)-9,9’-dimethylxanthene / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere; Industry scale
With
pyridine; trifluoromethylsulfonic anhydride; water; hydrogen; bromine; caesium carbonate; triethylamine; trifluoroacetic acid; potassium hydroxide; lithium hexamethyldisilazane;
1,1'-bis(diphenylphosphino)ferrocene; 4,5’-bis(diphenylphosphino)-9,9’-dimethylxanthene; 5%-palladium/activated carbon; palladium diacetate; triphenylphosphine;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;