Water → 2,5-Difluoro-3-methoxybenzaldehyde

HRID 1108094Notes

Reaction equation

HRID 1108094 reaction equation
[F-].[K+].I[CH3:4].[Si]([O:12][C:13]1[C:14]([F:22])=[C:15]([CH:18]=[C:19]([F:21])[CH:20]=1)[CH:16]=[O:17])(C(C)(C)C)(C)C.O>CN(C=O)C>[F:22][C:14]1[C:13]([O:12][CH3:4])=[CH:20][C:19]([F:21])=[CH:18][C:15]=1[CH:16]=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 522689Potassium FluorideHCID 113463223-Tert-butyldimethylsilyloxy-2,5-difluorobenzaldehyde

Product 1

HCID 112060352,5-Difluoro-3-methoxybenzaldehydeYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium fluoride (7.79 g, 134 mmol) and iodomethane (4.98 ml, 80 mmol) were added to a stirred solution of 3-tert-butyldimethylsilyloxy-2,5-difluorobenzaldehyde (19.45 g, 67 mmol) in DMF (100 ml) at room temperature. After 5 hr, the mixture was poured into water (100 ml) and extracted with ethyl acetate (200 ml). The extract was washed with water (100 ml), brine (100 ml), dried (magnesium sulfate) and evaporated. The residue was purified by column chromatography (silica gel) eluting with ethyl acetate/n-hexane (1/10) to give 8.58 g (74%) of the titled compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate (200 ml)
  2. washThe extract was washed with water (100 ml), brine (100 ml)
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated
  5. customThe residue was purified by column chromatography (silica gel)
  6. washeluting with ethyl acetate/n-hexane (1/10)

Sources & evidence

ORD record
ord-cefff10832474e37944bc1287a3313d6
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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