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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1971845Generated: November 1, 2026

Nitrogen → 3-(4-Fluoro-2-methylsulfanyl-phenyl)-acrylic acid methyl ester

https://huagongshe.com/reaction/1971845

Reaction equation

Participants

RoleNameHCIDCharge
ReactantNitrogenHCID 947—
ReactantMethyl AcrylateHCID 7294—
ReactantPotassium CarbonateHCID 11430—
Reactant(5-Fluoro-2-iodophenyl)(methyl)sulfaneHCID 58127007—
CatalystTetrabutylammonium ChlorideHCID 70681—
Catalystpalladium(II) acetateHCID 167845—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product3-(4-Fluoro-2-methylsulfanyl-phenyl)-acrylic acid methyl esterHCID 6692251689%

Reaction Steps

4-fluoro-1-iodo-2-methylsulfanyl-benzene (6.8 g 25.3 mmol), K2CO3 (9.9 g, 63.4 mmol), methyl acrylate (5.7 ml, 63.4 mmol), Tetra-n-butylammonium chloride (7.0 g, 25.3 mmol) and Pd(OAc)2 (1.1 g, 5.07 mmol) were mixed in DMF (150 ml). The mixture was heated at 50° C. under the atmosphere of N2 overnight, after which water was added and then extracted with ethyl acetate. The extracts were combined, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography to give the desired product (4.8 g, yield 89%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08431581B2
Source datasetuspto-grants-2013_04
ORD IDord-a58fd78498504445a13fd200f17eda87
Source noteuspto-grants-2013_04