Reaktion #730155

Reaktionsgleichung

4-chlorobiphenyl

(2-methylpropoxy)methyl boronic acid

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

cesium carbonate

→

title compound

Ausbeute 28.5%

4-Isobutoxymethyl-biphenyl

Ausbeute 28.5%

Lösungsmittel

water

1,4-dioxane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter the reaction mixture was cooled at room temperature
2. 2
   Filtrationfollowed by filtration
3. 3
   ExtraktionAfter the filtrate was extracted with ethyl acetate
4. 4
   Waschenthe organic layer was washed with water
5. 5
   Trocknenan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   workup.DISTILLATIONThe solvent was distilled off from the filtrate under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (heptane:ethylacetate=30:1)

Vorschrift

To a solution of 4-chlorobiphenyl (25 mg, 0.13 mmol) in 1,4-dioxane (1 ml) and water (100 μl) were added (2-methylpropoxy)methyl boronic acid (35 mg, 0.27 mmol), palladium (II) acetate (3.0 mg, 0.013 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (11 mg, 0.027 mmol), and cesium carbonate (130 mg, 0.40 mmol) at room temperature. The reaction mixture was stirred at 100° C. for 7 hours and 50 minutes under the nitrogen atmosphere. After the reaction mixture was cooled at room temperature, water was added to the mixture, followed by filtration using Celite. After the filtrate was extracted with ethyl acetate, the organic layer was washed with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was distilled off from the filtrate under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethylacetate=30:1) to obtain the title compound (9.0 mg, 0.037 mmol, 28%) as a colorless oil.

Quelle