Water → HCID 59803830, compound

HRID 253444Notes

Reaction equation

HRID 253444 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[Cs+].[Cs+].[F:16][C:17]([F:28])([F:27])[CH2:18]OS(C(F)(F)F)(=O)=O.O>CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:18][C:17]([F:28])([F:27])[F:16]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 748142-Chloro-4-fluorophenolHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 59803830HCID 59803830, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 2-chloro-4-fluorophenol (52, 1.58 g, 0.0108 mol) in N-methylpyrrolidinone (25.0 mL), cesium carbonate (7.02 g, 0.0215 mol) and trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester (2.50 g, 0.0108 mmol) were added under an atmosphere of nitrogen. The reaction was stirred at room temperature for 90 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 15% to 100% ethyl acetate in hexane to give a colorless oil (124, 2.10 g, 85.3%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 15% to 100% ethyl acetate in hexane
  7. customto give a colorless oil (124, 2.10 g, 85.3%)

Sources & evidence

ORD record
ord-eca673dc376d4e23b80df5b909dc9ec7
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

Loading…