Multi-step reaction with 10 steps
1.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / Inert atmosphere
1.2: Inert atmosphere
1.3: pH 4
2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere
2.2: 1.5 h / 0 - 20 °C / Inert atmosphere
3.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / tetrahydrofuran; hexane / 3.25 h / -78 - 0 °C / Inert atmosphere
3.2: 18 h / 0 - 20 °C / Inert atmosphere
4.1: bromine; pyridine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
5.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere
5.2: 2.5 h / -78 - 20 °C / Inert atmosphere
6.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere
6.2: 0.01 h / -78 °C / Inert atmosphere
7.1: N-ethyl-N,N-diisopropylamine; dimethyl sulfoxide / 2 h / 20 - 70 °C / Inert atmosphere
8.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
9.1: boron trichloride / dichloromethane / 1.5 h / -78 - 0 °C / Inert atmosphere
10.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 60 °C / Inert atmosphere
With
pyridine; 2,2,6,6-tetramethyl-piperidine; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; bromine; boron trichloride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/ja307207q