Multi-step reaction with 11 steps
1.1: triethylamine; sulfur / ethanol / 60 °C
2.1: tert.-butylnitrite / N,N-dimethyl-formamide / 1 h / 60 °C
3.1: N-Bromosuccinimide / N,N-dimethyl-formamide; tetrahydrofuran / 2 h / 20 °C
4.1: water / ethanol / 0.5 h / Reflux
4.2: pH 3
5.1: thionyl chloride; sodium tetrahydroborate / dimethyoxyethane / 1 h / 10 - 20 °C / Inert atmosphere; Reflux
6.1: manganese(IV) oxide / dichloromethane / 2.67 h / 20 °C
7.1: zinc(II) iodide / dichloromethane / 1.25 h / 0 - 20 °C / Inert atmosphere
8.1: water / 0.17 h / 0 - 20 °C
9.1: perchloric acid / 0.5 h / 0 °C
10.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 4.08 h / 95 °C / Inert atmosphere
11.1: ethanol / 4 h / Reflux
With
manganese(IV) oxide; sodium tetrahydroborate; N-Bromosuccinimide; thionyl chloride; tert.-butylnitrite; perchloric acid; water; sodium carbonate; sulfur; triethylamine; zinc(II) iodide;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; dimethyoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;