Reaktion #730150

Reaktionsgleichung

water

heptane

4-chlorobiphenyl

1,4-dioxane

water

cesium carbonate

→

title compound

Ausbeute 90.0%

4-Cyclopropylmethoxymethyl-biphenyl

Ausbeute 90.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige30 minutes
2. 2
   TemperaturAfter the reaction mixture was cooled at room temperature
3. 3
   Filtrationfollowed by filtration
4. 4
   WaschenThe separated organic layer was washed with an aqueous saturated sodium chloride solution
5. 5
   SonstigeThe organic layer was separated
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   SonstigeThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=30:1)

Vorschrift

To a mixture of 4-chlorobiphenyl (50 mg, 265 μmol) and 1,4-dioxane (2 ml) were added water (0.2 ml), cesium carbonate (259 mg, 795 μmol), potassium cyclopropylmethoxymethyl trifluoroborate (102 mg, 530 mol), palladium (II) acetate (5.95 mg, 27 μmol) and 2-dicycrohexylphospino-2′,6′-dimethoxybiphenyl (21.8 mg, 53.1 μmol). Then, the reaction mixture was stirred at 100° C. (external temperature) for 7 hours and 30 minutes. After the reaction mixture was cooled at room temperature, water and heptane 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=30:1) to obtain the title compound (57 mg, 239 μmol, 90%).

Quelle