Water → 2,6-Difluoro-3-hydroxybenzaldehyde

HRID 1964972Notes

Reaction equation

HRID 1964972 reaction equation
C([Si](C)(C)[O:6][C:7]1[C:8]([F:16])=[C:9]([C:12]([F:15])=[CH:13][CH:14]=1)[CH:10]=[O:11])(C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>CN(C)C=O>[F:16][C:8]1[C:7]([OH:6])=[CH:14][CH:13]=[C:12]([F:15])[C:9]=1[CH:10]=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 58086678HCID 58086678, compound

Product 1

HCID 5941112,6-Difluoro-3-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-(tert-butyl-dimethyl-silanyloxy)-2,6-difluoro-benzaldehyde (37, 3.50 g, 12.9 mmol) in N,N-dimethylformamide (50 mL) was added tetrabutylammonium fluoride trihydrate (4.40 g, 14.0 mmol). The reaction was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated to give crude compound 38 that was used in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-785f1126125f458faf0fd21b358059f6
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

Loading…