Multi-step reaction with 10 steps
1.1: sulfuric acid / 12 - 20 h / 50 - 55 °C
2.1: aluminum (III) chloride; bromine / chloroform / 6 h / 25 °C
3.1: potassium carbonate / bis(tri-t-butylphosphine)palladium(0) / 1,4-dioxane; water / 1.5 h / 75 °C
4.1: N-chloro-succinimide / tetrahydrofuran / 4 h / 70 °C
4.2: 2 h
5.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane / 12 h / 20 °C
6.1: hydrazine / tetrahydrofuran; methanol / 24 h / 20 °C
7.1: hydrogenchloride / 1,4-dioxane / 0.08 h
8.1: Selectfluor / water; acetonitrile / 12 h / 70 °C
9.1: sodium hydroxide / tetrahydrofuran; water / 1 h / 70 °C
9.2: acid / pH 4
10.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane / 12 h / 25 °C
With
hydrogenchloride; aluminum (III) chloride; sodium hydroxide; N-chloro-succinimide; sulfuric acid; bromine; potassium carbonate; Selectfluor; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; hydrazine;
bis(tri-t-butylphosphine)palladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; acetonitrile;