Multi-step reaction with 9 steps
1.1: iron(III) chloride; bromine / acetic acid / 5 h / 25 °C
2.1: sulfuric acid / 12 h / 50 °C
3.1: potassium carbonate / bis(tri-t-butylphosphine)palladium(0) / 1,4-dioxane; water / 1 h / 80 °C
4.1: N-Bromosuccinimide / tetrahydrofuran / 1 h / 70 °C
5.1: potassium carbonate / bis(tri-t-butylphosphine)palladium(0) / 1,4-dioxane; water / 12 h / 80 °C
6.1: hydrogen / palladium dihydroxide / methanol / 1 h / 760.05 Torr
7.1: sodium hydroxide / tetrahydrofuran; water / 1 h / 70 °C
7.2: acid / pH 4
8.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane / 2 h / 25 °C
9.1: hydrazine / tetrahydrofuran; methanol / 12 h / 25 °C
With
iron(III) chloride; sodium hydroxide; N-Bromosuccinimide; sulfuric acid; hydrogen; bromine; potassium carbonate; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; hydrazine;
palladium dihydroxide; bis(tri-t-butylphosphine)palladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetic acid;