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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 708940Generated: October 30, 2026

Sodium Carbonate → 4-[1-(4-Trifluoromethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]-benzaldehye

https://huagongshe.com/reaction/708940

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant1,4-DioxaneHCID 31275—
Reactant4-Formylphenylboronic AcidHCID 591073—
Reactant3-chloro-1-(4-trifluoromethoxyphenyl)-4,5-dihydro-1H-pyrazoleHCID 66956418—
CatalystHCID 178418476HCID 178418476—
SolventEthyl AcetateHCID 8857—
Product4-[1-(4-Trifluoromethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]-benzaldehyeHCID 5782447934.9%

Reaction Conditions

Temperature150 °C

Reaction Steps

A suspension of 3-chloro-1-(4-trifluoromethoxyphenyl)-4,5-dihydro-1H-pyrazole (114 mg, 0.43 mmol, 1.00 eq), 4-formylphenylboronic acid (97 mg, 0.65 mmol, 1.50 eq), bis(triphenylphosphine)palladium(II) dichloride (10 mg, 0.01 mmol, 0.03 eq), 2 M Na2CO3 (aq) (0.43 mL, 0.86 mmol, 2.0 eq), and 1,4-dioxane (5 mL) were heated at 150° C. in a microwave reaction vessel for 45 min. The cooled solution was then diluted with EtOAc (20 mL), filtered over Celite®, concentrated to dryness, and purified via chromatography (2:2:1, hexane:EtOAc:acetone) to afford the desired intermediate (50 mg, 0.15 mmol, 31%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09179681B2
Source datasetuspto-grants-2015_11
ORD IDord-9623784f49e140739e9b1eba6a6fe16e
Source noteuspto-grants-2015_11