3-Fluoro-4-hydroxymethylbenzonitrile → 3-Fluoro-4-formylbenzonitrile

HRID 2090197Notes

Reaction equation

HRID 2090197 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][OH:11])[C:5]#[N:6]>ClCCl.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=[O:11])[C:5]#[N:6]

Participants

4

Reactant 1

HCID 114805433-Fluoro-4-hydroxymethylbenzonitrile

Product 1

HCID 27831503-Fluoro-4-formylbenzonitrile

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

1.00 g (6.62 mmol) of 3-fluoro-4-(hydroxymethyl)benzonitrile are dissolved in 50 ml of dichloromethane, and 9.20 g (105.9 mmol) of manganese(IV) oxide are added. The mixture is stirred at room temperature overnight and then filtered through a short kieselguhr column. The solvent is distilled out under reduced pressure, and the residue is purified by column chromatography (silica gel, mobile phase: dichloromethane). 120 mg (12.1% of theory) of the title compound are obtained.

Workup

  1. filtrationfiltered through a short kieselguhr column
  2. distillationThe solvent is distilled out under reduced pressure
  3. customthe residue is purified by column chromatography (silica gel, mobile phase: dichloromethane)

Sources & evidence

ORD record
ord-dfd73bc8698242f3b3a620da6585df86
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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