Water → 2,5-Difluoro-3-methoxybenzaldehyde

HRID 1418483Notes

Reaction equation

HRID 1418483 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-b9c2b6490ff24506abac2b3758a3e051
Source dataset
uspto-grants-1999_03
Patent number
US05883106

Reaction notes

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