2-Fluoro-5-(hydroxymethyl)benzonitrile → 2-Fluoro-5-formylbenzonitrile

HRID 1357737Notes

Reaction equation

HRID 1357737 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH2:6][OH:7])#[N:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH:6]=[O:7])#[N:2]

Participants

4

Reactant 1

HCID 27739342-Fluoro-5-(hydroxymethyl)benzonitrile

Product 1

HCID 27695822-Fluoro-5-formylbenzonitrileYield 54.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A solution of the product from Example 82B (0.40 g, 2.6 mmol) in chloroform (50 mL) was treated with manganese dioxide (0.55 g, 7.8 mmol), stirred at room temperature overnight, filtered, solvent evaporated and the residue flash chromatographed over silica gel eluting with ethyl acetate:hexane (1:1) to provide 0.21 g 3-cyano-4-fluorobenzaldehyde.

Workup

  1. filtrationfiltered
  2. customsolvent evaporated
  3. customthe residue flash chromatographed over silica gel eluting with ethyl acetate:hexane (1:1)

Sources & evidence

ORD record
ord-e8da21326aaa4db88a74696d6cf7cadc
Source dataset
uspto-grants-2003_07
Patent number
US06593335B1

Reaction notes

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