Dimethylformamide → 2,2,2-trifluoro-N-(4-formyl-3,5-dimethylphenyl)acetamide

HRID 1514976Notes

Reaction equation

HRID 1514976 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[CH3:16].[Li]C.[Li+].[Br-].[Li]C(CC)C.CN([CH:29]=[O:30])C>C1COCC1.C(Cl)Cl.O>[F:12][C:11]([F:14])([F:13])[C:10]([NH:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([CH:29]=[O:30])=[C:3]([CH3:16])[CH:4]=1)=[O:15]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 21336351N-(4-bromo-3,5-dimethylphenyl)-2,2,2-trifluoroacetamideHCID 178418400CID 53628100HCID 178419607HCID 178419607, compound

Product 1

HCID 866328212,2,2-trifluoro-N-(4-formyl-3,5-dimethylphenyl)acetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-bromo-3,5-dimethylphenyl)-2,2,2-trifluoroacetamide (592 mg) in THF (10 mL) at −78° C. was added MeLi/LiBr (1.5M in Et2O, 1.87 mL) slowly. After 5 min, sec-BuLi (1.4M. in cyclohexane, 2.0 mL) was added slowly to the solution at −78° C. After 5 min DMF (0.31 mL) was added to the solution drowise at −78° C. then the mixture was warmed to room temperature. After 30 min the reaction mixture was partioned between water and CH2Cl2. The aqueous layer was extracted with CH2Cl2 and the combined organic layers were dried and filtered. Removal of the solvent under reduced pressure to gave a yellow solid which was purified by flash chromatography using hexanes/ethyl acetate (5:1) as eluent which gave 2,2,2-trifluoro-N-(4-formyl-3,5-dimethyl-phenyl)-acetamide as a light yellow solid. MS (ESI)m/z 246 (M+H).

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2
  2. customthe combined organic layers were dried
  3. filtrationfiltered
  4. customRemoval of the solvent under reduced pressure
  5. customto gave a yellow solid which
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-a85e9f62c9ab44edb837f092b1fde15e
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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