Reaktion #730156

Reaktionsgleichung

4-chlorobiphenyl

1,4-dioxane

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

potassium phosphate

→

title compound

Ausbeute 80.0%

Biphenyl-4-yl-methanol

Ausbeute 80.0%

Lösungsmittel

water

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturto reflux overnight under the nitrogen atmosphere
3. 3
   WaschenAfter the organic layer was washed with an aqueous saturated sodium chloride solution
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   SonstigeThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

Vorschrift

To a mixture of 4-chlorobiphenyl (23 mg, 0.12 mmol), 1,4-dioxane (2 ml) and water (200 μl) were added potassium acetoxymethyl trifluoroborate (44 mg, 0.24 mmol), palladium (II) acetate (14 mg, 0.061 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (50 mg, 0.12 mmol), and potassium phosphate (170 mg, 0.73 mmol) at room temperature. The reaction mixture was heated to reflux overnight under the nitrogen atmosphere. After the reaction mixture was cooled at room temperature, water and ethyl acetate were added to the mixture. After the organic layer was washed with an aqueous saturated sodium chloride solution, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (18 mg, 0.098 mmol, 80%).

Quelle