2-Iodobenzoic acid → 2-(4-Fluorophenoxy)benzoic acid

HRID 730161Notes

Reaction equation

HRID 730161 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[F:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1>CN(C)C=O.[Cu]>[F:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 69412-Iodobenzoic acidHCID 97324-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 30083672-(4-Fluorophenoxy)benzoic acidYield 44.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

100 g of potassium carbonate are added slowly to a mixture of 120 g of 2-iodobenzoic acid, 1 g of copper powder and 54.4 g of 4-fluorophenol in 200 ml of N,N-dimethylformamide. The mixture is heated at 160° C. for 4 hours and is then allowed to cool before evaporating. The residue is taken up in distilled water, acidified with aqueous 1N hydrochloric acid solution and then extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The desired product crystallizes from a diethyl ether/pentane mixture. 50 g of a white solid are obtained.

Workup

  1. temperatureto cool
  2. custombefore evaporating
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe desired product crystallizes from a diethyl ether/pentane mixture

Sources & evidence

ORD record
ord-9f7d6ca888394ca79b0799b77cc0f5d1
Source dataset
uspto-grants-2009_09
Patent number
US07582664B2

Reaction notes

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