Multi-step reaction with 9 steps
1: thionyl chloride / 0 - 60 °C
2: 4,4'-di-tert-butyl-2,2'-bipyridine / (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 80 °C / Inert atmosphere
3: copper dichloride / water; methanol / 90 °C
4: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 80 °C
5: toluene / 90 °C
6: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 50 °C
7: hydrogen / platinum(IV) oxide / ethanol / 3620.13 Torr
8: sodium hydroxide; water / methanol / 1 h
9: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 16 h / 0 - 80 °C
With
N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); diphenyl phosphoryl azide; water; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; 4,4'-di-tert-butyl-2,2'-bipyridine; sodium hydroxide; copper dichloride;
platinum(IV) oxide; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer;
In
tetrahydrofuran; methanol; tetrachloromethane; ethanol; water; toluene; acetonitrile;