Potassium Carbonate → (4-Fluorophenyl)methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-(trifluoromethyl)benzoate

HRID 1623736Notes

Reaction equation

HRID 1623736 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][O:1][C:2]2[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][C:3]=2[C:4]([O:6][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:5])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 111172032-hydroxy-5-(trifluoromethyl)benzoic Acid

Product 1

HCID 67107202(4-Fluorophenyl)methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-hydroxy-5-(trifluoromethyl)benzoic acid (may be prepared as described in Description 117; 2 g, 9.70 mmol) in acetone (50 ml) was added 1-(bromomethyl)-4-fluorobenzene (4.04 g, 21.35 mmol), potassium carbonate (4.02 g, 29.1 mmol) and the reaction was heated to reflux overnight. The mixture was filtered to remove the solid potassium carbonate. The solid was washed with acetone (50 ml). The organics were combined and evaporated under reduced pressure on a buchi to yield the title compound. The crude yellow oil was used directly without further purification. 4.1 g.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux overnight
  3. filtrationThe mixture was filtered
  4. customto remove the solid potassium carbonate
  5. washThe solid was washed with acetone (50 ml)
  6. customevaporated under reduced pressure on a buchi

Sources & evidence

ORD record
ord-9a0ed384c6be459896c48ef05a9bcfc3
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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