Tetrahydrofuran → 2-Nitro-4-(pentafluoroethyl)benzaldehyde

HRID 1689726Notes

Reaction equation

HRID 1689726 reaction equation
CN(C)/C=[CH:4]/[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19].C1C[O:25]CC1>P([O-])([O-])([O-])=O>[N+:18]([C:6]1[CH:7]=[C:8]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:10][C:5]=1[CH:4]=[O:25])([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 86623311HCID 86623311, compound

Product 1

HCID 573559322-Nitro-4-(pentafluoroethyl)benzaldehydeYield 52%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

To a solution of crude (E)-N,N-dimethyl-2-(2-nitro-4-(perfluoroethyl)phenyl)ethenamine (12.2 g, 39.2 mmol) in THF (300 mL) and pH 7.2 phosphate buffer (300 mL) was added NaIO4 (29.3 g, 137.2 mmol). After 2.5 hours an aliquot (˜0.3 mL) was removed, filtered and dried. The proton NMR of this sample indicated that the reaction was complete. The solids were removed and the filter cake was washed with EtOAc. The filtrate was washed with brine (2×100 mL), dried and concentrated. The concentrate was purified via flash chromatography (100% hexane to 5% EtOAc) to provide 2-nitro-4-(perfluoroethyl)benzaldehyde (5.4 g, 52%).

Workup

  1. customAfter 2.5 hours an aliquot (˜0.3 mL) was removed
  2. filtrationfiltered
  3. customdried
  4. customThe solids were removed
  5. washthe filter cake was washed with EtOAc
  6. washThe filtrate was washed with brine (2×100 mL)
  7. customdried
  8. concentrationconcentrated
  9. customThe concentrate was purified via flash chromatography (100% hexane to 5% EtOAc)

Sources & evidence

ORD record
ord-e5c74aed5e6d485980e45209a3e3327d
Source dataset
uspto-grants-2012_04
Patent number
US08153622B2

Reaction notes

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