Reaktion #74624

Reaktionsgleichung

1-(benzyloxy)-2-bromo-4-(trifluoromethoxy)benzene

(1-methyl-1H-pyrazol-5-yl)boronic acid

tricyclohexylphosphine

tripotassium phosphate

→

title compound

Ausbeute 70.0%

5-[2-(Benzyloxy)-5-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrazole

Ausbeute 70.0%

Lösungsmittel

dioxane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction mixture
2. 2
   Temperaturwas refluxed for 16 hours
3. 3
   Filtrationfiltering through Celite™
4. 4
   EinengenThe filtrate was concentrated in vacuo
5. 5
   workup.ADDITIONthe residue was diluted with ethyl acetate (100 mL)
6. 6
   ExtraktionThe organic extract
7. 7
   Waschenwas washed with water, saturated aqueous sodium chloride solution
8. 8
   Trocknendried over sodium sulfate
9. 9
   Einengenconcentrated in vacuo
10. 10
    SonstigePurification by silica gel column chromatography
11. 11
    Wascheneluting with ethyl acetate:hexane (1:9, by volume)

Vorschrift

A solution of 1-(benzyloxy)-2-bromo-4-(trifluoromethoxy)benzene (Preparation 535, 3.3 g, 9.5 mmol) and (1-methyl-1H-pyrazol-5-yl)boronic acid (Preparation 403, 1.2 g, 9.5 mmol) 1,4-in dioxane (25 mL) was degassed under argon for 30 minutes. Under argon, (1E,4E)-1,5-Diphenylpenta-1,4-dien-3-one-palladium (3:2) (348 mg, 0.38 mmol) and tricyclohexylphosphine (213 mg, 0.76 mmol) were added followed by the dropwise addition of a degassed solution of tripotassium phosphate (4 g, 19 mmol) in water (12.6 mL). Reaction mixture was refluxed for 16 hours before cooling to room temperature and filtering through Celite™. The filtrate was concentrated in vacuo and the residue was diluted with ethyl acetate (100 mL). The organic extract was washed with water, saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. Purification by silica gel column chromatography eluting with ethyl acetate:hexane (1:9, by volume) afforded the title compound, 2.3 g, 70% yield.

Quelle