3-(Trifluoromethyl)phenol → HCID 13770364, compound

HRID 1929623Notes

Reaction equation

HRID 1929623 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CC(=O)CC>[CH3:23][O:22][C:20](=[O:21])[CH2:19][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 13770364HCID 13770364, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 3-trifluoromethyl-phenol (5.000 g; 30.843 mmol), potassium carbonate (5.328 g; 38.554 mmol), and methyl bromoacetate (3.54 ml; 38.554 mmol) in butanone (210 ml) was heated at reflux for 3 h. Filtration, concentration to dryness under reduced pressure, and purification by FC (heptane/EA, 4/1) afforded (3-trifluoromethyl-phenoxy)-acetic acid methyl ester as a pale yellow oil (7.220 g; 99%). LC-MS: tR=0.95 min.; [M+H]+: no ionisation.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. filtrationFiltration, concentration to dryness
  4. customunder reduced pressure, and purification by FC (heptane/EA, 4/1)

Sources & evidence

ORD record
ord-8be0077c28f5442d8e85ca692a133334
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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