Methyl iodide → Methyl 4-fluoro-3-formylbenzoate

HRID 1966788Notes

Reaction equation

HRID 1966788 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH:11]=[O:12].CI.[C:15]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[CH3:15][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([CH:11]=[O:12])[CH:4]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27948184-fluoro-3-formylbenzoic acid

Product 1

HCID 53419692Methyl 4-fluoro-3-formylbenzoateYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoro-3-formyl-benzoic acid (800 mg, 4.8 mmol) in DMF (10 mL), are added MeI (0.35 mL, 5.7 mmol) and K2CO3 (790 mg, 5.7 mmol). The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is diluted with EtOAc (20 mL) and water (10 mL). The organic layer is separated, washed with brine, dried under anhy. Na2SO4 (500 mg), filtered and is concentrated. The residue is purified by silica gel flash chromatography with 0-20% EtOAc/heptane as the eluent. The product fractions are collected and concentrated to afford 4-fluoro-3-formyl-benzoic acid methyl ester (710 mg, 82%).

Workup

  1. customThe organic layer is separated
  2. washwashed with brine
  3. customdried under anhy
  4. filtrationNa2SO4 (500 mg), filtered
  5. concentrationis concentrated
  6. customThe residue is purified by silica gel flash chromatography with 0-20% EtOAc/heptane as the eluent
  7. customThe product fractions are collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-61ad802bd44c407daddfad28287297f5
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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