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

HRID 1386050Notes

Reaction equation

HRID 1386050 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-eca09c83a5364db3b29d773169eb1b7d
Source dataset
uspto-grants-2001_07
Patent number
US06265417B1

Reaction notes

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