Potassium Carbonate → 2-Bromo-4-chloro(2-fluoroethoxy)benzene

HRID 992481Notes

Reaction equation

HRID 992481 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].Br[CH2:11][CH2:12][F:13].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:11][CH2:12][F:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 696702-Bromo-4-chlorophenol

Product 1

HCID 184127582-Bromo-4-chloro(2-fluoroethoxy)benzeneYield 89%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred suspension of 2-bromo-4-chlorophenol (2.07 g, 10 mmol), 1-bromo-2-fluoroethane (1.52 g, 12 mmol) and potassium carbonate (1.65 g, 12 mmol) in 2-butanone (10 mL) was heated at reflux temperature for 16 hours. The suspension was allowed to cool and then filtered. The filtrate was concentrated in vacuo and then distilled in vacuo to afford the titled compound as a colorless oil (2.25 g, 89%): bp 80-82° C. @ 0.1 torr

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 16 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-63b3deb47297414d9d8a0e300db554c9
Source dataset
uspto-grants-2002_10
Patent number
US06469042B1

Reaction notes

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