Multi-step reaction with 12 steps
1.1: periodic acid; iodine; acetic acid; sulfuric acid / water / 6 h / 80 °C
2.1: hydrogenchloride; sodium nitrite / water / 16.5 h / 0 - 20 °C
3.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / 1,2-dichloro-ethane / 16 h / 80 °C / Darkness
4.1: calcium carbonate; water / 1,4-dioxane / 10 h / Reflux
5.1: thionyl chloride / dichloromethane / 0 - 20 °C / Inert atmosphere
6.1: TurboGrignard / tetrahydrofuran / 0.17 h / -20 °C / Inert atmosphere
6.2: 16 h / -20 - 20 °C / Inert atmosphere
7.1: potassium carbonate / tetrahydrofuran; methanol / 16 h / 20 °C / Inert atmosphere
8.1: sodium acetate; palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / 12 h / 80 °C / 11636.1 Torr / Inert atmosphere; Autoclave
9.1: diisobutylaluminium hydride / toluene; dichloromethane / 1 h / -78 °C / Inert atmosphere
10.1: hydroxylamine hydrochloride; sodium acetate / water; methanol / 18 h / 20 °C / Inert atmosphere
11.1: N-chloro-succinimide / N,N-dimethyl-formamide / 1 h / 45 °C / Darkness; Inert atmosphere
11.2: 16 h / 20 °C / Darkness; Inert atmosphere
12.1: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
With
hydrogenchloride; 1,1'-bis-(diphenylphosphino)ferrocene; N-chloro-succinimide; N-Bromosuccinimide; TurboGrignard; thionyl chloride; 2,2'-azobis(isobutyronitrile); sulfuric acid; hydroxylamine hydrochloride; water; iodine; sodium acetate; palladium diacetate; diisobutylaluminium hydride; potassium carbonate; acetic acid; periodic acid; calcium carbonate; sodium nitrite;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;