Acetonitrile → HCID 561417, compound

HRID 1675583Notes

Reaction equation

HRID 1675583 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 resulting mixture was heated under reflux for 10 hours. Thereafter, the reaction mixture which had been cool to near room temperature was concentrated under reduced pressure. Hydrochloric acid was added to the residue, followed by extraction 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, and 7.5 g of 4-benzyloxy-3-fluoro-5-methoxybenzaldehyde was obtained.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 10 hours
  3. concentrationwas concentrated under reduced pressure
  4. additionHydrochloric acid was added to the residue
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-675b8dae3bc849cfa30ccd82c63747fb
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

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