Multi-step reaction with 7 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere
1.2: -78 - 20 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; toluene / 0.17 h / 20 °C / Inert atmosphere
2.2: 6 h / 90 °C / Inert atmosphere
3.1: copper(l) iodide; triethylamine; triphenylphosphine / tetrahydrofuran / 0.08 h / Inert atmosphere
3.2: 70 °C / Inert atmosphere
4.1: toluene-4-sulfonic acid / methanol; dichloromethane / 20 °C
5.1: potassium carbonate; potassium iodide / acetone / 48 h / Reflux; Inert atmosphere
6.1: water; potassium hydroxide / tetrahydrofuran; ethanol / Reflux
7.1: 2,6-di-tert-butyl-4-methyl-phenol; N,N-dimethyl-aniline / 1,4-dioxane / 4 h / 50 °C / Inert atmosphere
With
copper(l) iodide; n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; water; potassium carbonate; toluene-4-sulfonic acid; N,N-dimethyl-aniline; triethylamine; triphenylphosphine; potassium iodide; potassium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; acetone; toluene;
2.1: Suzuki coupling / 2.2: Suzuki coupling / 3.1: Sonogashira coupling / 3.2: Sonogashira coupling;
DOI:10.1039/c2jm31367g