Water → 2,6-Difluoro-3-hydroxybenzaldehyde

HRID 1261124Notes

Reaction equation

HRID 1261124 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-5e224851350b4bebbcda337204cbae58
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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