Diethyl Sulfate → 3-Chloro-4-fluorophenetole

HRID 2095624Notes

Reaction equation

HRID 2095624 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:10](OS(OCC)(=O)=O)[CH3:11].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 757903-Chloro-4-fluorophenol

Product 1

HCID 27737033-Chloro-4-fluorophenetole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-chloro-4-fluorophenol (2.0 g, 13.7 mmol), diethylsulfate (1.58 mL, 17.8 mmol) and K2CO3 (9.4 g, 68.5 mmol) in acetone (20 mL) was heated under refluxed for 3 h. The reaction mixture was filtered and concentrated. The residue was diluted with ethyl acetate (50 mL), washed with water (30 mL) and brine. The organic layer was dried (Na2SO4) and concentrated to give the title compound as a liquid. 1H NMR (CDCl3, 400 MHz): δ=1.39 (t, 3H, J=7.2 Hz), 3.97 (q, 2H, J=7.2 Hz), 6.71-6.74 (m, 1H), 6.89-6.91 (m, 1H), 7.02 (t, 1H, J=8.8 Hz).

Workup

  1. temperaturewas heated
  2. temperatureunder refluxed for 3 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. additionThe residue was diluted with ethyl acetate (50 mL)
  6. washwashed with water (30 mL) and brine
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1d69fe330c7c483785a8c4dc4a4b67f5
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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