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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1532273Generated: October 30, 2026

Formic Acid → 3-{[3-Fluoro-4-(methylsulfonyl)-phenyl]methylene}-2,4-pentanedione

https://huagongshe.com/reaction/1532273

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormic AcidHCID 284—
ReactantPiperidineHCID 8082—
ReactantAcetylacetoneHCID 31261—
Reactant3-Fluoro-4-methanesulfonylbenzaldehydeHCID 21251732—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product3-{[3-Fluoro-4-(methylsulfonyl)-phenyl]methylene}-2,4-pentanedioneHCID 9838737—

Reaction Conditions

Temperature20 °C

Reaction Steps

To a solution containing 0.93 g 3-fluoro-4-methylsulfonylbenzaldehyde, 0.05 ml piperidine and 0.02 ml formic acid in 20 ml DMF was added 1.04 ml 2,4-pentanedione with stirring at 20° C. The solution was stirred overnight at 20° C. and poured into water. The product was extracted with ethyl acetate and washed with water and evaporated to dryness in vacuo. The residue was crystallized from methanol, yield 0.48 g (30%), mp. 140-143° C. 1H-NMR (DMSO-d6, 400 MHz): 2.28 (s, 3 H, CH3), 2.50 (s, 3 H, CH3), 3.36 (s, 3 H, CH3), 7.47 (m, 1 H, Ar), 7.93 (m, 2 H, Ar), 7.76 (s, 1 H, CH).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06201027B1
Source datasetuspto-grants-2001_03
ORD IDord-3440cfa0cadc48578545e8061e426742
Source noteuspto-grants-2001_03