Potassium Carbonate → HCID 86666217, compound

HRID 705930Notes

Reaction equation

HRID 705930 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.F[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 177506914-Chloro-2,6-difluorophenol

Product 1

HCID 86666217HCID 86666217, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-chloro-2,6-difluorophenol (5.0 g, 30.4 mmol), 4-fluorobenzaldehyde (3.1 mL, 28.9 mmol) in DMF (30 mL), was added K2CO3 (5.0 g, 36.2 mmol). The mixture was heated at 100° C. overnight. After cooling, the reaction mixture was diluted in water, extracted with EA. The organic phase was washed with water and brine, dried over Na2SO4, concentrated, purified by flash chromatography to afford the title compound (5.4 g, 20.10 mmol, 66.1% yield) as a colorless oil. LCMS: rt=3.52 min, [M+H+]=269

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EA
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c75bfd4db0144390beb3c9105dbfde5b
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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