Dimethylformamide → Methyl 3-fluoro-4-methoxybenzoate

HRID 906068Notes

Reaction equation

HRID 906068 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1O)[C:5]([OH:7])=[O:6].[C:12](=O)([O-])[O-].[Cs+].[Cs+].IC.CN(C)[CH:22]=[O:23]>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:23][CH3:22])[C:5]([O:7][CH3:12])=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 1604563-Fluoro-4-hydroxybenzoic acid

Product 1

HCID 592848Methyl 3-fluoro-4-methoxybenzoateYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-fluoro-4-hydroxybenzoic acid (500 mg, 3.2 mmol), cesium carbonate (3.1 g, 9.6 mmol) and iodomethane (440 μl, 7.0 mmol) in dimethylformamide (7 mL) was stirred at room temperature for 4 hours. The mixture was diluted with ethyl acetate and washed with 5% aqueous lithium chloride, 1N aqueous sodium hydroxide, brine, then dried over anhydrous sodium sulfate. Filtration and concentration afforded 534 mg, 2.9 mmol (92%) of methyl 3-fluoro-4-(methyloxy)benzoate. MS (EI) for C9H9FO3: 185 (MH+).

Workup

  1. washwashed with 5% aqueous lithium chloride, 1N aqueous sodium hydroxide, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-eae0840a07e74c64b86ef201413dda1e
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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