Ethylparaben → Ethyl 4-(3-(trifluoromethyl)pyridin-2-yloxy)benzoate

HRID 1880020Notes

Reaction equation

HRID 1880020 reaction equation
F[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1>CS(C)=O.O>[F:9][C:8]([F:11])([F:10])[C:7]1[C:2]([O:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:28][CH:29]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8434EthylparabenHCID 10796Cesium carbonateHCID 27832962-Fluoro-3-(trifluoromethyl)pyridine

Product 1

HCID 59326875Ethyl 4-(3-(trifluoromethyl)pyridin-2-yloxy)benzoate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-Fluoro-3-(trifluoromethyl)pyridine (848 mg, 5137 μmol), cesium carbonate (2008 mg, 6164 μmol) and ethyl 4-hydroxybenzoate (854 mg, 5137 μmol) were combined in DMSO (12 mL) and heated to 80° C. overnight. After complete disappearance of starting material, the mixture was cooled to RT and diluted with water and extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to give the desired product which was used without further purification.

Workup

  1. temperatureAfter complete disappearance of starting material, the mixture was cooled to RT
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0fb50e8e0d2144d2aa6c1e4e4ec0294f
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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