Potassium Carbonate → Methyl 5-fluoro-2-{[2-(trifluoromethyl)benzyl]oxy}benzoate

HRID 1672645Notes

Reaction equation

HRID 1672645 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[F:13][C:14]([F:24])([F:23])[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17]Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:17][C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[C:14]([F:13])([F:23])[F:24])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 890281-(Chloromethyl)-2-(trifluoromethyl)benzeneHCID 2783186Methyl 5-fluoro-2-hydroxybenzoate

Product 1

HCID 57864353Methyl 5-fluoro-2-{[2-(trifluoromethyl)benzyl]oxy}benzoateYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 7.50 g (44.08 mmol) of methyl 5-fluoro-2-hydroxybenzoate in 40 ml of dry acetonitrile is mixed with 9.44 g (48.49 mmol) of 2-trifluoromethylbenzyl chloride and 18.28 g (132.25 mmol) of anhydrous potassium carbonate and heated under reflux for 12 hours. The mixture is then cooled, filtered, washed with dichloromethane and concentrated, and the residue is purified by chromatography (silica gel; mobile phase: cyclohexane/ethyl acetate 5:1). 9.18 g (28 mmol, 89% purity, 56% yield) of the title compound are obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. temperatureThe mixture is then cooled
  4. filtrationfiltered
  5. washwashed with dichloromethane
  6. concentrationconcentrated
  7. customthe residue is purified by chromatography (silica gel; mobile phase: cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-722a7e85975f4859b072ba308e98f1b5
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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