Potassium Carbonate → HCID 10799668, compound

HRID 1470635Notes

Reaction equation

HRID 1470635 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].F[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[O:9][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 943922,6-Difluorophenol

Product 1

HCID 10799668HCID 10799668, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of 2,6-difluorophenol (1.0 g, 8 mmol), potassium carbonate (3.29 g, 24.2 mmol) and 4-fluoro benzaldehyde (1.36 g 10.4 mmol) in dry DMF (50 mL) was stirred at 100° C. overnight under nitrogen atmosphere. After the reaction is completed it was cooled to room temperature and poured in to ice cold water. The mixture was extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with water (50 mL×2), brine, then dried over anhydrous sodium sulphate and concentrated. The resulting residue was purified by column chromatography using 3% ethyl acetate in hexane to obtain the title compound.

Workup

  1. additionpoured in to ice cold water
  2. extractionThe mixture was extracted with ethyl acetate (100 mL×2)
  3. washThe combined organic layers were washed with water (50 mL×2), brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-a286caf5cd4a4d2ba290d1b2d76398c2
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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