Multi-step reaction with 9 steps
1.1: boron tribromide / dichloromethane / 0 °C / Inert atmosphere; Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 5 °C
2.2: 1820 h / 20 °C
3.1: magnesium; ethylene dibromide / tetrahydrofuran / 50 - 65 °C / Inert atmosphere
3.2: 1 h / 5 °C / Inert atmosphere
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 5 °C / Inert atmosphere
4.2: 5 - 20 °C / Inert atmosphere
5.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran; ethanol / 0 - 4 °C
6.1: 1H-imidazole / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere
7.1: Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; water / N,N-dimethyl-formamide; tert-butyl alcohol / 42 h / 0 - 10 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere
9.1: pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / Heating
With
1H-imidazole; sodium tetrahydroborate; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; boron tribromide; sodium hydride; potassium carbonate; magnesium; acetic acid; ethylene dibromide;
In
tetrahydrofuran; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol;
DOI:10.1002/jlcr.1791