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

HRID 410154Notes

Reaction equation

HRID 410154 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

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-13b06cb5e2604c3899dfecbd82f9429d
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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