Multi-step reaction with 9 steps
1.1: trifluoroacetic acid; sodium nitrite; sulfuric acid / water / 1 h / 18 °C / Cooling with ice
1.2: 10 °C / Cooling with ice
2.1: 144 h / 20 °C / Cooling with ice; Darkness
3.1: potassium hydroxide / methanol / 6 h / Reflux
4.1: n-butyllithium / hexane; 1,2-dimethoxyethane / 1 h / -75 - -35 °C
4.2: 1 h / -78 °C
4.3: 2 h / -35 - 20 °C
5.1: bromine; acetic acid / chloroform / 2 h / Reflux
6.1: water / 3 h / 140 °C / Microwave irradiation
7.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere; Sealed flask
8.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1 h / 20 °C
9.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
With
n-butyllithium; lithium hydroxide monohydrate; sulfuric acid; water; bromine; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium hydroxide; sodium nitrite;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; chloroform; water; N,N-dimethyl-formamide;