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

HRID 987380Notes

Reaction equation

HRID 987380 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 2B (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-0f17795abd5f4cc1ba9ef83d75bb531e
Source dataset
uspto-grants-2003_10
Patent number
US06632418B2

Reaction notes

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