Dimethylformamide → 2,4-Difluoro-3-methoxybenzaldehyde

HRID 1446463Notes

Reaction equation

HRID 1446463 reaction equation
C([N-]C(C)C)(C)C.[Li+].C1C[O:12][CH2:11]C1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[O:22][CH3:23].CN(C=O)C>C(OCC)(=O)C.O>[F:14][C:15]1[C:16]([O:22][CH3:23])=[C:17]([F:21])[CH:18]=[CH:19][C:20]=1[CH:11]=[O:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 27368972,6-Difluoroanisole

Product 1

HCID 37202372,4-Difluoro-3-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium diisopropyl amide (1.5M cyclohexane solution, 5.6 mL) was added dropwise to a THF (10 mL) solution of 2,6-difluoroanisole (1.00 g) at −72° C. under nitrogen atmosphere, and the reaction solution was agitated for 30 minutes. DMF (2.7 mL) was added to the reaction mixture, the reaction solution was agitated for 30 minutes at −78° C., and then agitated at room temperature for 1 hour. Water and ethyl acetate were added to the reaction mixture, and the organic layer was partitioned. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent:hexane-ethyl acetate system) and 433 mg of the title compound was obtained.

Workup

  1. stirringthe reaction solution was agitated for 30 minutes at −78° C.
  2. stirringagitated at room temperature for 1 hour
  3. customthe organic layer was partitioned
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (elution solvent:hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-0869a51db5184392886383b04191913f
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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