Water → 6-Chloro-2-fluoro-3-(2,2,2-trifluoro-ethoxy)-benzaldehyde

HRID 1964995Notes

Reaction equation

HRID 1964995 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[C:4]([F:14])[CH:3]=1.C([Li])CCC.CN(C)[CH:22]=[O:23].O>C1COCC1.C(=O)=O.CC(C)=O>[Cl:1][C:2]1[C:3]([CH:22]=[O:23])=[C:4]([F:14])[C:5]([O:8][CH2:9][C:10]([F:12])([F:11])[F:13])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 595067484-Chloro-2-fluoro-1-(2,2,2-trifluoroethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 595068296-Chloro-2-fluoro-3-(2,2,2-trifluoro-ethoxy)-benzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 18522661Acetone cardiceSolvent

Procedure

To 4-Chloro-2-fluoro-1-(2,2,2-trifluoro-ethoxy)-benzene (522, 0.80 g, 3.5 mmol) in THF (20 mL), cooled in dry ice/acetone bath and under an atmosphere of nitrogen, was slowly added n-butyllithium (1.60 M in Hexane, 2.30 mL). After an hour, N,N-dimethylformamide (0.298 mL, 3.85 mmol) was added to the reaction. After 30 minutes, the reaction was allowed to reach room temperature and was stirred for 10 minutes. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give the compound (523, 450 mg, 50%).

Workup

  1. waitAfter an hour
  2. customto reach room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 20% ethyl acetate in hexane
  9. customto give the compound (523, 450 mg, 50%)

Sources & evidence

ORD record
ord-e34738b8d06f41fa8da2d0f3ad28d112
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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