Multi-step reaction with 11 steps
1.1: toluene-4-sulfonic acid / benzene / Reflux
2.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 °C
2.2: -78 - 20 °C
3.1: ammonium cerium (IV) nitrate / acetonitrile; water / 1 h / 70 °C
4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C
4.2: 20 °C
5.1: potassium acetate / 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere
6.1: potassium phosphate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 90 °C / Inert atmosphere
7.1: N-iodo-succinimide / acetonitrile / 1 h / 20 °C
8.1: potassium phosphate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 90 °C / Inert atmosphere
9.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 45 °C
10.1: N-Bromosuccinimide / acetonitrile / 1 h / 20 °C
11.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 100 °C / Inert atmosphere
With
potassium phosphate; N-Bromosuccinimide; N-iodo-succinimide; ammonium cerium (IV) nitrate; hydrogen; potassium acetate; lithium diisopropyl amide;
1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon; toluene-4-sulfonic acid;
In
tetrahydrofuran; 1,4-dioxane; water; ethyl acetate; acetonitrile; benzene;