Dimethylformamide → 2-Methoxy-5-(trifluoromethoxy)benzaldehyde

HRID 1267881Notes

Reaction equation

HRID 1267881 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.C([Li])(C)(C)C.CN([CH:22]=[O:23])C>O1CCCC1>[CH3:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:12])([F:13])[F:1])=[CH:9][C:8]=1[CH:22]=[O:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27249731-Methoxy-4-(trifluoromethoxy)benzeneHCID 178418306HCID 178418306, compound

Product 1

HCID 27833642-Methoxy-5-(trifluoromethoxy)benzaldehydeYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(trifluoromethoxy)anisole (5.0 g, 26 mmol) in tetrahydrofuran (100 mL) cooled to −78° C. was slowly added a solution of tert-butyllithium in pentanes (23 mL, 1.7M, 39 mmol). The resulting solution was stirred at −78° C. for 30 minutes, before N,N′-dimethylformamide (8 mL, 104 mmol) was added. The solution was allowed to stir to ambient temperature and was then quenched with saturated aqueous ammonium chloride (100 mL). The suspension formed was extracted with ethyl acetate (2×100 mL) and the extracts dried (MgSO4). Concentration gave a yellow oil which was purified by silica chromatography to give the title compound as an oil (4.13 g, 18.8 mmol).

Workup

  1. additionwas added
  2. customwas then quenched with saturated aqueous ammonium chloride (100 mL)
  3. customThe suspension formed
  4. extractionwas extracted with ethyl acetate (2×100 mL)
  5. dry with materialthe extracts dried (MgSO4)
  6. concentrationConcentration
  7. customgave a yellow oil which
  8. customwas purified by silica chromatography

Sources & evidence

ORD record
ord-49f38f5c50f74b0ebbf7752bb7007ae5
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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