Methyl iodide → 3,5-Difluoro-2-methoxybenzaldehyde

HRID 1757163Notes

Reaction equation

HRID 1757163 reaction equation
[F:1][C:2]1[C:3]([OH:11])=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=[O:6].[C:12](=O)([O-])[O-].[K+].[K+].CI>C(#N)C>[F:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27793743,5-difluoro-2-hydroxybenzaldehyde

Product 1

HCID 5989943,5-Difluoro-2-methoxybenzaldehydeYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,5-Difluoro-2-hydroxybenzaldehyde in the form of a crude product (corresponding to 0.35 mol) was dissolved in 800 ml of acetonitrile. 110 g (0.8 mol) of potassium carbonate and 61 ml (0.96 mol) of methyl iodide were added thereto, and the mixture was heated under reflux for 5 hr. After cooling the mixture, insolubles were removed by filtration, and the mother liquor was concentrated. 1.3 l of ether was added to the concentrate, and the mixture was washed twice with 500 ml of water. Then, the mixture was washed with a saturated saline solution, and the ether layer was dried over anhydrous magnesium sulfate. The solvent was distilled off in vacuo to prepare 39.6 g (yield: 66%) of the intended product (in two states).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hr
  3. temperatureAfter cooling the mixture, insolubles
  4. customwere removed by filtration
  5. concentrationthe mother liquor was concentrated
  6. addition1.3 l of ether was added to the concentrate
  7. washthe mixture was washed twice with 500 ml of water
  8. washThen, the mixture was washed with a saturated saline solution
  9. dry with materialthe ether layer was dried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-887adb99a5054b34ae3da583b3c2ca55
Source dataset
uspto-grants-1995_08
Patent number
US05444083

Reaction notes

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