Methyl iodide → Methyl 3-fluoro-2-methylbenzoate

HRID 2301125Notes

Reaction equation

HRID 2301125 reaction equation
[F:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:12](=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>CN(C)C=O>[CH3:12][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[C:3]=1[CH3:11]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2466823-Fluoro-2-methylbenzoic acid

Product 1

HCID 21752566Methyl 3-fluoro-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Fluoro-2-methyl-benzoic acid (4.8 g, 31 mmol), potassium carbonate (4.3 g, 31 mmol) and methyl iodide (4.5 g, 31 mmol) were stirred at room temperature for 17.5 hours in anhydrous N,N-dimethylformamide (50 ml). The reaction solution was mixed with ethyl acetate, washed with water and saturated brine and then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation from the organic, layer under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 4.8 g (27 mmol, 87% in yield) of the title compound.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customThe solvent was removed by evaporation from the organic, layer under a reduced pressure
  4. customthe thus obtained material was separated
  5. custompurified by a silica gel column chromatography
  6. customto obtain

Sources & evidence

ORD record
ord-6f10e80fff854466bb6addb329ad0ddd
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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