Iodoethane → HCID 15751976, compound

HRID 1678807Notes

Reaction equation

HRID 1678807 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.I[CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:9][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 759283,5-Difluorophenol

Product 1

HCID 15751976HCID 15751976, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3,5-difluoro-phenol (10.0 g, 76.87 mmol, 1.0 equiv) and iodo-ethane (28.77 g, 14.91 mL, 184.49 mmol, 2.4 equiv) in acetone (150 mL) was added portionwise potassium carbonate (31.87 g, 230.6 mmol, 3.0 equiv) and the reaction mixture heated to reflux for 6 h. The reaction mixture was filtered, the filtrate poured into ice water and then extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4 and concentrated by evaporation under reduced pressure yielding 7.60 g (63%) of the title compound.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 6 h
  3. filtrationThe reaction mixture was filtered
  4. additionthe filtrate poured into ice water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7c93deff200a46999d4d7edb02e00c1e
Source dataset
uspto-grants-2011_08
Patent number
US08008503B2

Reaction notes

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