Cesium fluoride → 5-Bromo-2,3-difluorobenzaldehyde

HRID 34022Notes

Reaction equation

HRID 34022 reaction equation
[Br:1][C:2]1[C:3]([Si](C)(C)C)=[C:4]([F:11])[C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[F-].[Cs+]>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 2

HCID 25953Cesium fluorideHCID 230701765-Bromo-2,3-difluoro-4-(trimethylsilyl)benzaldehyde

Product 1

HCID 230701825-Bromo-2,3-difluorobenzaldehydeYield 75.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 18.0 g of 5-bromo-2,3-difluoro-4-trimethylsilanyl benzaldehyde in 20 mL of N,N-dimethylformamide and 2 mL of water was added 1.63 g of cesium fluoride at room temperature, and stirred at this temperature for 1 hour. After diluting with ethyl acetate, the organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated, to afford 10.26 g of the title compound as a colorless oil.

Workup

  1. washthe organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fddcc1bba83a4ad4804828b8fcf6c8d4
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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