Dimethylformamide → Methyl 4-fluoro-3-methoxybenzoate

HRID 1243216Notes

Reaction equation

HRID 1243216 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5](C(O)=O)=[CH:4][C:3]=1O.[C:12](=[O:15])([O-])[O-:13].[K+].[K+].[CH3:18]I.CN(C)[CH:22]=[O:23]>>[CH3:18][O:13][C:12](=[O:15])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([O:23][CH3:22])[CH:4]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5936354-Fluoro-3-hydroxybenzoic acid

Product 1

HCID 592847Methyl 4-fluoro-3-methoxybenzoate

Procedure

4-Fluoro-3-hydroxybenzoic acid (4.33 g, 27.7 mmol) (Aldrich) was dissolved in anhydrous dimethylformamide (Aldrich). Potassium carbonate (38.3 g, 277 mmol) and methyl iodide (8.6 mL, 138.5 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred overnight. After filtration, the solution was washed with water and extracted with ethyl acetate. The layers were separated and the organic layer was successively washed with water, 1 N aqueous sodium hydroxide, water and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 4-fluoro-3-methoxybenzoic acid methyl ester as a pale yellow oil that solidified upon standing. (Yield 4.72 g, 92%).

Workup

  1. filtrationAfter filtration
  2. washthe solution was washed with water
  3. extractionextracted with ethyl acetate
  4. customThe layers were separated
  5. washthe organic layer was successively washed with water, 1 N aqueous sodium hydroxide, water and brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-33256250c24848d58e57140986e74fef
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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