Cesium carbonate → HCID 57719050, compound

HRID 1985264Notes

Reaction equation

HRID 1985264 reaction equation
[F:1][C:2]([C:5]1[C:10](O)=[CH:9][CH:8]=[C:7](C)[CH:6]=1)([F:4])[F:3].Br[CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C([O-])([O-])=[O:22].[Cs+].[Cs+]>CN(C=O)C>[CH2:18]([O:17][C:15](=[O:16])[CH:14]([O:22][C:8]1[CH:7]=[CH:6][C:5]([C:2]([F:1])([F:3])[F:4])=[CH:10][CH:9]=1)[CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79040Ethyl 2-bromopropionateHCID 21901956HCID 21901956, compound

Product 1

HCID 57719050HCID 57719050, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of trifluromethyl-p-cresol (9.74 g, 60.1 mmol), ethyl 2-bromopropionate (10.9 g, 60.1 mmol) and Cs2CO3 (39.15 g, 120 mmol) in DMF (450 mL) was heated at 90° C. under N2 for 16 h. The reaction was cooled and filtered using Et2O to rinse the solids. The filtrate was washed with 1 N HCl (200 mL) and water. The organic layer was dried (Na2SO4) and the solvent removed in vacuo to afford 19.03 g of crude product that was purified by flash chromatography using 6:1 hexanes:acetone to afford 13.96 g (89%) 2-(4-trifluoromethyl-phenoxy)-propionic acid ethyl ester. Rf=0.63 (1:1 hexanes:acetone). 1NMR.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. washto rinse the solids
  4. washThe filtrate was washed with 1 N HCl (200 mL) and water
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customthe solvent removed in vacuo
  7. customto afford 19.03 g of crude product that
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-93d9d2539f9843c88d0ca776c3027dd7
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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