(4-Fluoro-3-iodophenyl)methanol → 4-Fluoro-3-iodobenzaldehyde

HRID 478277Notes

Reaction equation

HRID 478277 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[I:10]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[I:10]

Participants

4

Reactant 1

HCID 23497488(4-Fluoro-3-iodophenyl)methanol

Product 1

HCID 103080734-Fluoro-3-iodobenzaldehydeYield 29.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6212ChloroformSolvent

Procedure

The product from Example 30B (6.4 g, 26 mmol) in chloroform (300 mL) was treated with manganese dioxide (4.5 g, 50 mmol), stirred overnight, treated with an additional portion of manganese dioxide (2.25 g), stirred overnight, filtered and concentrated. The residue was purified by flash chromatography over silica gel (ethyl acetate/hexane 1:4) to provide 1.9 g of the title compound.

Workup

  1. stirringstirred overnight
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography over silica gel (ethyl acetate/hexane 1:4)

Sources & evidence

ORD record
ord-ceb960621f224c55bfbede30bda91587
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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