Selenium Dioxide → 6-(2-(Trifluoromethyl)phenyl)picolinaldehyde

HRID 2309739Notes

Reaction equation

HRID 2309739 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[C:13]([CH3:15])[CH:12]=[CH:11][CH:10]=1.[Se](=O)=[O:19]>O1CCOCC1>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[C:13]([CH:15]=[O:19])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24007Selenium Dioxide2×HCID 21275753Pyridine, 2-methyl-6-[2-(trifluoromethyl)phenyl]-

Product 1

HCID 201846876-(2-(Trifluoromethyl)phenyl)picolinaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

0.6 g of 6-(2-trifluoromethylphenyl)-2-methylpyridine was dissolved in 50 ml of 1,4-dioxane, 0.43 g of selenium dioxide (Aldrich, Gold Label) was added and the mixture was refluxed for 48 hours. A further 0.7 g, selenium dioxide and 50 ml dioxane were added and refluxing was continued for a further 48 hours. The solids were removed by filtration and the dioxane evaporated to afford crude 6-(2-trifluoromethylphenyl)-2-pyridinecarboxaldehyde.

Workup

  1. temperaturethe mixture was refluxed for 48 hours
  2. temperaturerefluxing
  3. customThe solids were removed by filtration
  4. customthe dioxane evaporated

Sources & evidence

ORD record
ord-657aa89e52c54645b7e9db75624c07f6
Source dataset
uspto-grants-1987_09
Patent number
US04696938

Reaction notes

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