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

HRID 1058678Notes

Reaction equation

HRID 1058678 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 8B (6.4 g, 26 mmol) in chloroform (300 mL) was treated with manganese dioxide (4.5 g, 50 mmol) and stirred overnight. Additional manganese dioxide (2.25 g) was added to the reaction mixture and stirred overnight. The slurry was filtered and the solvent evaporated. The crude product 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. filtrationThe slurry was filtered
  3. customthe solvent evaporated
  4. customThe crude product was purified by flash chromatography over silica gel (ethyl acetate/hexane 1:4)

Sources & evidence

ORD record
ord-b5f2daee67cc4c7aa81b32674c2d058a
Source dataset
uspto-grants-2003_02
Patent number
US06518279B2

Reaction notes

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