Multi-step reaction with 11 steps
1.1: sodium nitrite; hydrogenchloride / 0.5 h / 0 °C
1.2: 0.83 h / 0 - 90 °C
2.1: potassium carbonate / acetone / 5 h / Reflux
3.1: sodium hydroxide / water; methanol / 2 h / Reflux
4.1: Vilsmeier reagent / dichloromethane / 0.5 h / 0 - 20 °C
4.2: 12 h / 0 - 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 6.5 h / 0 - 20 °C
6.1: palladium diacetate; triphenylphosphine; sodium acetate / N,N-dimethyl-formamide / 8 h / 100 °C / Inert atmosphere
7.1: boron tribromide / dichloromethane / 3 h / 0 °C / Inert atmosphere
8.1: pyridine / dichloromethane / 2 h / 0 - 20 °C
9.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / 1,4-dioxane / 3 h / 120 °C / Inert atmosphere
10.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / N,N-dimethyl-formamide / 3 h / 120 °C / Inert atmosphere
11.1: sodium hydroxide / water; ethanol / 3 h / 80 °C
With
pyridine; hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; tetrakis(triphenylphosphine) palladium(0); Vilsmeier reagent; potassium acetate; sodium acetate; palladium diacetate; boron tribromide; sodium hydride; potassium carbonate; triphenylphosphine; sodium hydroxide; sodium nitrite;
In
1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
6.1: |Heck Reaction;
DOI:10.1021/jm3002394