Selenium Dioxide → 6-(2-Bromophenyl)picolinaldehyde

HRID 2309735Notes

Reaction equation

HRID 2309735 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[CH:10][CH:9]=1.[Se](=O)=[O:16]>O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([CH:14]=[O:16])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 201846906-(2-Bromophenyl)-2-methylpyridine

Product 1

HCID 201846796-(2-Bromophenyl)picolinaldehydeYield 54.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-(2-bromophenyl)-2-methylpyridine (3.5 g) was dissolved in 150 ml 1,4-dioxane. Selenium dioxide (Aldrich, Gold Label, 2.0 g) was added and the mixture was refluxed for a total of 50 hours. The solids were removed by filtration and the mixture was diluted with ether. The solution was washed several times with water, dried over magnesium sulfate, filtered and evaporated to afford 2.0 g of crude 6-(2-bromophenyl)-2-pyridinecarboxaldehyde as a yellow semi-solid.

Workup

  1. temperaturethe mixture was refluxed for a total of 50 hours
  2. customThe solids were removed by filtration
  3. additionthe mixture was diluted with ether
  4. washThe solution was washed several times with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-75e7260bb95d44a1aa0c2334fa9a0529
Source dataset
uspto-grants-1987_09
Patent number
US04696938

Reaction notes

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