Multi-step reaction with 11 steps
1: bromine / dichloromethane / 36 h / 0 - 20 °C / Inert atmosphere
2: triethylamine / palladium diacetate; 1,1'-bis(diphenylphosphino)ferrocene / ethanol / 70 °C / Inert atmosphere
3: bromine; pyridine / dichloromethane / 2 h / 0 - 20 °C
4: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -50 - -5 °C / Inert atmosphere
5: potassium carbonate / acetone / 1 h / Reflux; Inert atmosphere
6: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Cooling with ice; Inert atmosphere
7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 5 - 20 °C / Inert atmosphere
8: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; water / 0.1 h / 80 °C / Inert atmosphere
9: hydrogen / 5% rhodium on activated aluminium oxide / methanol / 3 h / 65 °C / 3750.38 Torr
10: hydrogenchloride / dichloromethane; water / 16 h / 20 °C
11: caesium carbonate / palladium diacetate; 4,5’-bis(diphenylphosphino)-9,9’-dimethylxanthene / 1,4-dioxane / 20 h / 100 °C / Inert atmosphere
With
pyridine; hydrogenchloride; hydrogen; bromine; sodium carbonate; potassium carbonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane;
bis-triphenylphosphine-palladium(II) chloride; 1,1'-bis(diphenylphosphino)ferrocene; 4,5’-bis(diphenylphosphino)-9,9’-dimethylxanthene; 5% rhodium on activated aluminium oxide; palladium diacetate;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; acetone;