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

HRID 503169Notes

Reaction equation

HRID 503169 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-1cbd791e3eb6452594788b53b6c89a15
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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