Acetonitrile → HCID 561417, compound

HRID 602029Notes

Reaction equation

HRID 602029 reaction equation
C(#N)C.[F:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:14][CH3:15])[C:12]=1[OH:13])[CH:8]=[O:9].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:16]([O:13][C:12]1[C:11]([O:14][CH3:15])=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[F:4])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 5984523-Fluoro-4-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 561417HCID 561417, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 40 ml of acetonitrile were added 7.3 g of 3-fluoro-4-hydroxy-5-methoxybenzaldehyde, 8.8 g of benzyl bromide, 16.8 g of cesium carbonate and 10 ml of DMF, and the mixture obtained was heated under reflux for 10 hours. The reaction mixture was concentrated under reduced pressure. Hydrochloric acid was added to the residue and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 7.5 g of 4-benzyloxy-3-fluoro-5-methoxybenzaldehyde represented by the formula:

Workup

  1. customthe mixture obtained
  2. temperaturewas heated
  3. temperatureunder reflux for 10 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionHydrochloric acid was added to the residue
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9aa2b853590b4077a74671659e0524ae
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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