Multi-step reaction with 12 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C
2.1: aluminum (III) chloride / dichloromethane / 0.17 h / 25 °C
2.2: 25 °C
3.1: sodium tetrahydroborate; trifluoroacetic acid / dichloromethane / 0 - 25 °C / Inert atmosphere
4.1: caesium carbonate / tetrahydrofuran; methanol / 2 h / 70 °C
5.1: ozone / N,N-dimethyl-formamide / 0.13 h / -5 °C
6.1: hydrogenchloride / acetone / 24 h
7.1: hydrogenchloride / water / 24 h
8.1: potassium acetate / ethanol / 5 h / Reflux
9.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 8 h / Inert atmosphere; Reflux
10.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; toluene / 12 h / Inert atmosphere; Reflux
11.1: hydrogen / palladium on activated charcoal / tetrahydrofuran / 2 h
12.1: potassium acetate / toluene / 2 h / 20 °C
12.2: 80 °C
With
hydrogenchloride; aluminum (III) chloride; sodium tetrahydroborate; oxalyl dichloride; hydrogen; potassium acetate; potassium carbonate; caesium carbonate; ozone; N,N-dimethyl-formamide; trifluoroacetic acid;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
10.1: Suzuki Coupling;