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

HRID 1837060Notes

Reaction equation

HRID 1837060 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-00669de1260044c9a777ecffe9f7f508
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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