Multi-step reaction with 11 steps
1.1: sodium cyanide / water; methanol / 20 - 70 °C
2.1: 6 h / 120 °C / Inert atmosphere
3.1: ammonia / dichloromethane; water / 0.5 h / -25 °C / Inert atmosphere
4.1: copper(ll) sulfate pentahydrate / ethanol; water / 0.5 h / Inert atmosphere; Reflux
5.1: trifluoroacetic acid / ethanol / Inert atmosphere; Reflux
6.1: trifluoroacetic acid / dichloromethane / 3 h / Inert atmosphere; Reflux
7.1: sodium nitrite; hydrogen bromide / water / 1.25 h / 0 °C
8.1: bronze powder / dimethyl sulfoxide / 16 h / Inert atmosphere
9.1: n-butyllithium / hexane; diethyl ether / -78 °C / Inert atmosphere
9.2: 1.25 h / -78 - 20 °C / Inert atmosphere
10.1: diethyl ether / 4 h / 0 - 20 °C
11.1: potassium carbonate / N,N-dimethyl-formamide / 20 - 65 °C
With
sodium cyanide; bronze powder; n-butyllithium; copper(ll) sulfate pentahydrate; ammonia; hydrogen bromide; potassium carbonate; trifluoroacetic acid; sodium nitrite;
trifluoroacetic acid;
In
methanol; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;