4-Fluoro-3-[(3-fluorophenyl)-hydroxymethyl)-5-methoxybenzonitrile → HCID 22260967, compound

HRID 1610125Notes

Reaction equation

HRID 1610125 reaction equation
[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[OH:13]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:12](=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1

Participants

4

Reactant 1

HCID 222606574-Fluoro-3-[(3-fluorophenyl)-hydroxymethyl)-5-methoxybenzonitrile

Product 1

HCID 22260967HCID 22260967, compoundYield 9.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7.0 g of 4-fluoro-3-[(3-fluorophenyl)-hydroxymethyl]-5-methoxybenzonitrile in 70 ml toluene was added 11.1 g of activated manganese dioxide at room temperature. After stirring at 60° C. for one day, the manganese dioxide was filtered off through Celite. The solvent was removed and the crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:3), to give 640 mg of the title compound as colorless crystals.

Workup

  1. filtrationthe manganese dioxide was filtered off through Celite
  2. customThe solvent was removed
  3. customthe crude product was purified
  4. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-3769358f5fb4425888c05337ca6d39c7
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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