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

HRID 1862416Notes

Reaction equation

HRID 1862416 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[I:10]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[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 12B (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. 1H NMR (300 MHz, CDCl3) δ 7.23 (t, 1H), 7.89 (m, 1H), 8.32 (dd, 1H), 9.91 (s, 1H).

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-22b13402673145949cfb7ae4547c0928
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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