Butyl bromide → 1-Butoxy-3,5-difluorobenzene

HRID 1741552Notes

Reaction equation

HRID 1741552 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH3:5].[F:6][C:7]1[CH:8]=[C:9]([OH:14])[CH:10]=[C:11]([F:13])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:2]([O:14][C:9]1[CH:8]=[C:7]([F:6])[CH:12]=[C:11]([F:13])[CH:10]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 759283,5-Difluorophenol

Product 1

HCID 190101831-Butoxy-3,5-difluorobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 1-bromobutane (11.0 g, 0.08 mol) in acetone (30 ml) was added dropwise to a stirred, refluxing mixture of 3,5-difluorophenol (9.1 g, 0.07 mol) and potassium carbonate (30 g, 0.2 mol) in acetone (200 ml). The stirred mixture was heated under reflux for 24 h (glc analysis revealed absence of starting material). The product was extracted into ether (twice), and the combined ethereal extracts were washed with water, 5% sodium hydroxide, water and dried (MgSO4). Most of the solvent was removed in vacuo, and after the removal of the final amount of solvent and the excess of 1-bromobutane at atmospheric pressure, the residue was distilled to yield a colourless liquid.

Workup

  1. temperaturerefluxing
  2. temperatureThe stirred mixture was heated
  3. temperatureunder reflux for 24 h (glc analysis revealed absence of starting material)
  4. extractionThe product was extracted into ether (twice), and the combined ethereal extracts
  5. washwere washed with water, 5% sodium hydroxide, water
  6. dry with materialdried (MgSO4)
  7. customMost of the solvent was removed in vacuo
  8. customafter the removal of the final amount of solvent
  9. distillationthe excess of 1-bromobutane at atmospheric pressure, the residue was distilled
  10. customto yield a colourless liquid

Sources & evidence

ORD record
ord-5f9c616dc41a4fbdab9a8ecbb9042829
Source dataset
uspto-grants-1994_08
Patent number
US05334327

Reaction notes

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