Selenium Dioxide → 6-(2-Fluorophenyl)pyridine-2-carbaldehyde

HRID 2309737Notes

Reaction equation

HRID 2309737 reaction equation
[F: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>[F: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 212757582-(2-Fluorophenyl)-6-methylpyridine

Product 1

HCID 201846836-(2-Fluorophenyl)pyridine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.0 g of 6-(2-fluorophenyl)-2-methylpyridine was dissolved in 250 ml of 1,4-dioxane. Selenium dioxide (2.67 g, Aldrich Gold Label) was added and the mixture was reluxed for 6 days. The solids were removed by filtration and the dioxane was evaporated. The crude 6-(2-fluorophenyl)-2-pyridinecarboxaldehyde was purified by chromatography on silica gel to afford pure 6-(2-fluorophenyl)-2-pyridinecarboxaldehyde.

Workup

  1. customThe solids were removed by filtration
  2. customthe dioxane was evaporated
  3. customThe crude 6-(2-fluorophenyl)-2-pyridinecarboxaldehyde was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-475e5e75db414212a90837a0e5d814a5
Source dataset
uspto-grants-1987_09
Patent number
US04696938

Reaction notes

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