Ethylene Glycol → 2-(2,4,5-Trifluorophenoxy)ethanol

HRID 1295711Notes

Reaction equation

HRID 1295711 reaction equation
CC([O-])(C)C.[K+].F[C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=1[F:16].[CH2:17]([OH:20])[CH2:18][OH:19].CCOC(C)=O>CS(C)=O>[F:16][C:9]1[CH:10]=[C:11]([F:15])[C:12]([F:14])=[CH:13][C:8]=1[O:19][CH2:18][CH2:17][OH:20]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8857Ethyl Acetate2×HCID 94741,2,4,5-TetrafluorobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 693650882-(2,4,5-Trifluorophenoxy)ethanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

t-BuOK (3.0 g, 27 mmol) was added to a mixture of 1,2,4,5-tetrafluorobenzene (2.0 g, 13.3 mmol) and ethylene glycol (7.5 mL, 133 mmol) in DMSO (50 mL) and heated at 80° C. for 1 h and then at 60° C. overnight. EtOAc was added and the resulting solution was washed several times with water. The organic layer was dried (Na2SO4) and concentrated carefully in vacuo at 30° C. to furnish 1.5 g (containing ˜14% EtOAc) of the title compound as a white semisolid. NMR analysis supports the stated structure. This material was used directly in the next step.

Workup

  1. customat 60° C.
  2. customovernight
  3. washthe resulting solution was washed several times with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated carefully in vacuo at 30° C.
  6. customto furnish

Sources & evidence

ORD record
ord-cf455d6ee5e6485bbb67450ab174862e
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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