Multi-step reaction with 9 steps
1.1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 1 h / 0 - 20 °C
2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 1 h / 20 - 25 °C
3.1: potassium carbonate / tetrahydrofuran / 6 h / -10 - 35 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / -10 °C / Inert atmosphere
5.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h
6.1: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / Inert atmosphere
7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
8.1: caesium carbonate / tris-(dibenzylideneacetone)dipalladium(0); XPhos / xylene / 12 h / 120 °C / Inert atmosphere
9.1: water; lithium hydroxide / tetrahydrofuran; methanol / 12 h / 20 °C
9.2: pH 7 / Cooling with ice
With
N-chloro-succinimide; lithium aluminium tetrahydride; 18-crown-6 ether; carbon tetrabromide; hydroxylamine hydrochloride; potassium tert-butylate; water; potassium carbonate; caesium carbonate; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; lithium hydroxide;
tris-(dibenzylideneacetone)dipalladium(0); XPhos;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; xylene;