Multi-step reaction with 12 steps
1.1: iodine / 16 h / 25 °C
2.1: N-Bromosuccinimide / dichloromethane / 16 h / 25 °C
3.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 16 h / 100 °C
4.1: phosphorus tribromide / 1,2-dichloro-ethane / 1 h / Reflux
5.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 16 h / 100 °C
6.1: hydrogen / palladium 10% on activated carbon / methanol / 16 h / 25 °C
7.1: Dess-Martin periodane / dichloromethane / 0.5 h / 25 °C
8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
9.1: toluene-4-sulfonic acid / toluene / 1 h / 110 °C
10.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 20 °C
10.2: -78 - 20 °C
11.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 16 h / 100 °C
12.1: hydroxylamine hydrochloride; potassium hydroxide / ethanol; water / 48 h / 65 °C
With
N-Bromosuccinimide; hydroxylamine hydrochloride; hydrogen; iodine; phosphorus tribromide; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; trifluoroacetic acid; potassium hydroxide; lithium hexamethyldisilazane;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; toluene;