Reaktion #730151

Reaktionsgleichung

cesium carbonate

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

4-chlorobiphenyl

1,4-dioxane

→

title compound

Ausbeute 38.0%

2-(Biphenyl-4-ylmethoxy)ethanol

Ausbeute 38.0%

Lösungsmittel

dichloromethane

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter the reaction mixture was cooled at room temperature
2. 2
   Filtrationfollowed by filtration
3. 3
   WaschenThe separated organic layer was washed with an aqueous saturated sodium chloride solution
4. 4
   SonstigeThe organic layer was separated
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1 NH silica gel)

Vorschrift

To a mixture of 4-chlorobiphenyl (15 mg, 79.5 μmol) and 1,4-dioxane (1.5 ml) were added water (0.15 ml), cesium carbonate (117 mg, 358 μmol), sodium (2-hydroxyethoxy)methyl trifluoroborate (19.7 mg, 119 mol), palladium (II) acetate (5.37 mg, 23.9 μmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (19.6 mg, 47.7 μmol). Then, the reaction mixture was stirred at 100° C. (external temperature) for 13 hours. After the reaction mixture was cooled at room temperature, water and dichloromethane were added to the mixture, followed by filtration using Celite. The separated organic layer was washed with an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1 NH silica gel) to obtain the title compound (6.8 mg, 30 μmol, 38%).

Quelle