Multi-step reaction with 8 steps
1.1: sodium hydride / ethanol; pentane; tetrahydrofuran; mineral oil / Cooling with ice
1.2: 20 - 40 °C / Reflux
1.3: pH 1 - 2
2.1: ethanol; sodium / 0.25 h / -5 - 0 °C
2.2: 0 - 20 °C
3.1: hydrazine hydrate / ethanol / 20 °C
4.1: potassium carbonate / N,N-dimethyl-formamide / 0.33 h
4.2: 20 - 30 °C
5.1: hydrogen / ethanol; tetrahydrofuran / 724.03 Torr
6.1: water; hydrogen bromide / 1.25 h / 130 °C
7.1: potassium tert-butylate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 110 °C / Inert atmosphere
8.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 0.17 h / 140 °C / Microwave irradiation
With
ethanol; potassium tert-butylate; water; hydrogen bromide; hydrogen; sodium; sodium hydride; potassium carbonate; hydrazine hydrate;
tris-(dibenzylideneacetone)dipalladium(0); tetrakis(triphenylphosphine) palladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;
In
tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; toluene; mineral oil; pentane;