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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2095857Generated: November 1, 2026

Tetrahydrofuran → 5-Bromo-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

https://huagongshe.com/reaction/2095857

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantN-bromobutanimideHCID 67184—
ReactantSodium BicarbonateHCID 516892—
Reactant1-(4-Fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrileHCID 66968925—
SolventAcetonitrileHCID 6342—
SolventEthyl AcetateHCID 8857—
Product5-Bromo-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrileHCID 5815856786%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a solution of 1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (1 g, 4.05 mmol) in acetonitrile (10 mL)/tetrahydrofuran (5 mL) was added N-bromosuccinimide (792 mg, 4.46 mmol), and the mixture was stirred at 60° C. overnight. After cooling to room temperature, saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was washed with diethyl ether and collected by filtration to give the title compound (1.07 g, 86%) as a slightly yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08445509B2
Source datasetuspto-grants-2013_05
ORD IDord-ebf3ebaf7671419a91cdc7b0b827824e
Source noteuspto-grants-2013_05