Réaction #716555

Équation de réaction

water

methyl 4-cyano-2-hydroxy-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

1-(4-(chloromethyl)phenyl)-1H-pyrazole

tripotassium phosphate trihydrate

→

title compound

Rendement 22.5%

methyl 4-cyano-2-hydroxy-3-methyl-5-[4-(1H-pyrazol-1-yl)benzyl]benzoate

Rendement 22.5%

Solvants

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   SéchageThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Autrethe solvent was evaporated under reduced pressure
4. 4
   AutreThe residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether)

Mode opératoire

To a solution of methyl 4-cyano-2-hydroxy-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (3.50 g) in 1,4-dioxane (30.0 mL) were added 1-(4-(chloromethyl)phenyl)-1H-pyrazole (2.12 g), tripotassium phosphate trihydrate (5.90 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.34 g), and the mixture was stirred at 90° C. for 16 hr under nitrogen atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (0.86 g).

Source