Dimethylformamide → HCID 13861691, compound

HRID 1016796Notes

Reaction equation

HRID 1016796 reaction equation
C([Si](C)(C)[O:6][C:7]1[C:8]([F:23])=[C:9]([CH:12]=[C:13](O[Si](C(C)(C)C)(C)C)[CH:14]=1)[CH:10]=[O:11])(C)(C)C.[F-].[K+].[CH3:28]I.CN([CH:33]=[O:34])C>O>[F:23][C:8]1[C:7]([O:6][CH3:28])=[CH:14][C:13]([O:34][CH3:33])=[CH:12][C:9]=1[CH:10]=[O:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 522689Potassium FluorideHCID 138616903,5-Bis{[tert-butyl(dimethyl)silyl]oxy}-2-fluorobenzaldehyde

Product 1

HCID 13861691HCID 13861691, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the 3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-fluoro-benzaldehyde (3.0 g, 7.8 mmol) obtained in Example 251.1, potassium fluoride (1.81 g, 31.2 mmol), methyl iodide (1.17 ml, 18.7 mmol) and DMF (25 ml) was stirred for 2 h. at room temperature. Water (25 ml) was added and the mixture was extracted with diethyl ether. The organic phase was washed with water, dried, filtered and concentrated. The residue was purified by chromatography (SiO2, cyclohexane/EtOAc 18:1=>1:1). There was obtained 0.87 g (60%) of 2-fluoro-3,5-dimethoxy-benzaldehyde as a colorless solid.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic phase was washed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (SiO2, cyclohexane/EtOAc 18:1=>1:1)

Sources & evidence

ORD record
ord-ac1f107763c64cdda82b8d6767f2fbff
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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