Multi-step reaction with 9 steps
1.1: 18 h / Reflux
2.1: aluminum (III) chloride / dichloromethane / 0.17 h / -78 °C
2.2: 25.75 h / -78 - 20 °C
3.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 85 °C
4.1: caesium carbonate / acetonitrile / 16 h / 20 °C / Inert atmosphere
5.1: lithium hydroxide / water; tetrahydrofuran; methanol / 16 h / 40 °C
5.2: pH 4
6.1: thionyl chloride / dichloromethane / 16 h / 20 °C / Inert atmosphere
7.1: potassium acetate; XPhos / bis(dibenzylideneacetone)-palladium(0) / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere
8.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; 1,4-dioxane; water / 16.5 h / Inert atmosphere; Reflux
9.1: hydrogenchloride / ethyl acetate; 1,4-dioxane; water; methanol / 2 h / Inert atmosphere
9.2: pH 6.5
With
hydrogenchloride; aluminum (III) chloride; N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); potassium acetate; sodium carbonate; caesium carbonate; lithium hydroxide; XPhos;
tetrakis(triphenylphosphine) palladium(0); bis(dibenzylideneacetone)-palladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
4.1: Buchwald reaction;