Iodoethane → HCID 15751976, compound

HRID 1170694Notes

Reaction equation

HRID 1170694 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 aceton (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. 1H NMR (300 MHz, CDCl3): δ1.41 (t, J=7.5 Hz, 3H), 3.99 (q, J=7.5 Hz, 2H), 6.36-6.43 (m, 3H).

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-5db83d622371434d882ba82d7970b654
Source dataset
uspto-grants-2010_11
Patent number
US07825258B2

Reaction notes

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