Multi-step reaction with 9 steps
1.1: toluene-4-sulfonic acid / benzene / Reflux
2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C
2.2: -78 - 20 °C
2.3: 6 h / 70 °C
3.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C
3.2: -78 - 20 °C
4.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; 1,1'-bis-(diphenylphosphino)ferrocene / 1,4-dioxane / 16 h / 80 °C
5.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 16 h / 90 °C
6.1: hydrogen / palladium on activated charcoal / tetrahydrofuran / 16 h / 50 °C / 760.05 Torr
6.2: 24 h / Reflux
7.1: N-iodo-succinimide / acetonitrile / 0.5 h / 20 °C
8.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 16 h / 90 °C
9.1: N-Bromosuccinimide / dichloromethane; acetonitrile / 0.5 h / 20 °C
With
potassium phosphate; N-Bromosuccinimide; N-iodo-succinimide; hydrogen; potassium acetate; lithium diisopropyl amide;
1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium on activated charcoal; toluene-4-sulfonic acid;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile; benzene;