3-Fluorophenol → 2-[(3-fluorophenoxy)methyl]oxirane

HRID 1060354Notes

Reaction equation

HRID 1060354 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15]([CH:17]1[O:19][CH2:18]1)Br>CC(C)=O>[CH2:15]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[CH:17]1[O:19][CH2:18]1

Participants

5

Reactant 3

HCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 18430Epibromohydrin

Product 1

HCID 99896102-[(3-fluorophenoxy)methyl]oxiraneYield 44.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-fluorophenol (1.8 g, 16.1 mmol) in acetone (100 mL) was treated with potassium carbonate (6.65 g, 48.2 mmol) and refluxed under nitrogen for 15 minutes. Epibromohydrin (4.4 g, 32.1 mmol) was then added by syringe, and the mixture was refluxed 3 hours. The mixture was cooled and filtered, and the filtrate evaporated to dryness. The residue was partitioned between ether/water, and the layers separated. The ether layer was washed with saturated NaCl, dried over sodium sulfate and evaporated. The resulting oil was distilled under vacuum to give 1.2 g of 3-fluorophenyl glycidyl ether.

Workup

  1. temperaturerefluxed under nitrogen for 15 minutes
  2. temperaturethe mixture was refluxed 3 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated to dryness
  6. customThe residue was partitioned between ether/water
  7. customthe layers separated
  8. washThe ether layer was washed with saturated NaCl
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. distillationThe resulting oil was distilled under vacuum

Sources & evidence

ORD record
ord-1499f7c9ebc44b0080aa64e8c43ed97e
Source dataset
uspto-grants-2003_02
Patent number
US06521667B1

Reaction notes

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