Water → HCID 28604051, compound

HRID 1436328Notes

Reaction equation

HRID 1436328 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1F)[CH:11]=[O:12].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1.O>CN(C=O)C>[F:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([O:18][CH3:17])[CH:20]=1)[CH:11]=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 90073-MethoxyphenolHCID 10796Cesium carbonateHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 28604051HCID 28604051, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Cesium carbonate (2.757 g, 8.44 mmol) was added to a solution of 3,4-difluoro-benzaldehyde (1.0 g, 7.037 mmol) and 3-methoxyphenol (875 mg, 7.05 mmol) dissolved in DMF (20 mL). The reaction was heated to 120° C. for 24 hours. The reaction mixture was then poured into 300 mL of water and extracted 3 times with 60 mL of ethyl acetate. The combined organic layers were washed with water (2 times), brine, and dried over sodium sulfate. The organic layer was filtered and concentrated under reduced pressure. 3-Fluoro-4-(3-methoxy-phenoxy)-benzaldehyde (1.0 g) was isolated using flash silica gel and eluting with 10% ethyl acetate and heptane.

Workup

  1. extractionextracted 3 times with 60 mL of ethyl acetate
  2. washThe combined organic layers were washed with water (2 times), brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic layer was filtered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04aa1f329b83457190f25137c86e8bee
Source dataset
uspto-grants-2009_11
Patent number
US07618996B2

Reaction notes

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