Multi-step reaction with 16 steps
1.1: silver nitrate; iodine / dichloromethane / 14 h / 20 °C / Inert atmosphere
2.1: copper dichloride; tert.-butylhydroperoxide / acetonitrile; water / 16 h / 20 - 50 °C
3.1: thionyl chloride / dichloromethane / 2 h / 20 °C / Inert atmosphere; Reflux
4.1: water; tetrahydrofuran / 0.08 h
4.2: 2 h / 0 °C
5.1: lithium iodide monohydrate / ethyl acetate / 48 h / 20 °C / Reflux
6.1: [bis(acetoxy)iodo]benzene / dichloromethane / 0.17 h / 20 °C
7.1: potassium hydroxide / water; methanol / 0.25 h / -20 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 3 h / 20 °C / Inert atmosphere
9.1: triethylamine; tetrakis(triphenylphosphine) palladium(0) / acetonitrile; tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
10.1: triethylamine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
11.1: lithium borohydride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere
12.1: triethylamine; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere
13.1: lithium iodide monohydrate / ethyl acetate / 8 h / 20 °C / Reflux
14.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere
15.1: iodine; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 20 °C / Inert atmosphere
15.2: 0.5 h
16.1: diisobutylaluminium hydride / toluene / 20 h / 20 °C / Inert atmosphere
With
2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; lithium borohydride; tetrakis(triphenylphosphine) palladium(0); thionyl chloride; lithium iodide monohydrate; [bis(acetoxy)iodo]benzene; iodine; diisobutylaluminium hydride; silver nitrate; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium hydroxide; copper dichloride;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; acetonitrile;
4.1: |Schotten-Baumann Reaction;
DOI:10.1002/chem.201402323