Water → 4-Bromo-5-fluoro-1-methylpyridin-2(1H)-one

HRID 1191854Notes

Reaction equation

HRID 1191854 reaction equation
CI.[C:3](=[O:6])([O-])[O-].[K+].[K+].[Br:9][C:10]1[C:15]([F:16])=[CH:14][NH:13][C:12](=O)[CH:11]=1.O>CN(C)C=O>[Br:9][C:10]1[C:15]([F:16])=[CH:14][N:13]([CH3:12])[C:3](=[O:6])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 267469844-Bromo-5-fluoropyridin-2(1H)-one

Product 1

HCID 596356714-Bromo-5-fluoro-1-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (0.9 mL) was added to a mixture of potassium carbonate (2.34 g) and 4-bromo-5-fluoro-1H-pyridin-2-one (2.50 g) in dimethylformamide (25 mL) at room temperature. The mixture was stirred at room temperature overnight and then water was added. The resulting mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried (MgSO4). The solvent was evaporated to afford the crude title compound that was recrystallized from Et2O. Yield: 1.22 g (45% of theory); Mass spectrum (ESI+): m/z=206/208 (Br) [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washthe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-cf70dca0c4794a31bd275326cf4561a6
Source dataset
uspto-grants-2014_03
Patent number
US08680093B2

Reaction notes

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