Tetrahydrofuran → 4-Fluoro-2-nitrobenzaldehyde

HRID 583072Notes

Reaction equation

HRID 583072 reaction equation
CN(C=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14])C.C1C[O:19]CC1>>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]=[O:19])=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 538945262-(4-Fluoro-2-nitrophenyl)-N,N-dimethylethen-1-amine

Product 1

HCID 762264-Fluoro-2-nitrobenzaldehyde

Procedure

N,N-Dimethyl-2-(4-fluoro-2-nitrophenyl)ethenylamine (6.72 g, 32 mmol) and NaIO4 (20.53 g, 96 mmol) were stirred in 50% aqueous THF (160 ml) at room temperature for 1.5 hours. The mixture was filtered in a celite pad and eluted with EtOAc. The organic layer was washed with NaHCO3 (saturated solution, 3×100 ml), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (50% CH2Cl2 /hexane) affording 4-fluoro-2-nitro benzaldehyde as an orange oil.

Workup

  1. filtrationThe mixture was filtered in a celite pad
  2. washeluted with EtOAc
  3. washThe organic layer was washed with NaHCO3 (saturated solution, 3×100 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (50% CH2Cl2 /hexane)

Sources & evidence

ORD record
ord-afa506e468954b398f57fc3dc7d09258
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

Loading…