Methanol → 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-iodo benzoic acid methyl ester

HRID 910365Notes

Reaction equation

HRID 910365 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[C:16]([I:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:28]O>S(=O)(=O)(O)O>[CH3:28][O:19][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)([C:24]([F:26])([F:25])[F:27])[O:13][N:12]=2)=[CH:15][C:16]=1[I:23]

Participants

4

Reactant 2

HCID 887MethanolHCID 667851434-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-iodo benzoic acid

Product 1

HCID 667844134-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-iodo benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

In a solution of 0.60 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-iodo benzoic acid synthesized similarly to Steps 1 to 4 of Synthetic Example 4 in 10 ml of methanol, 2 drops of concentrated sulfuric acid was added, and stirred under reflux with heat for 20 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was neutralized with 10 ml of saturated sodium hydrogen carbonate aqueous solution, then extracted with ethyl acetate (10 ml×2). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:4), and 0.56 g of the aimed product was obtained as colorless oily substance.

Workup

  1. temperatureunder reflux
  2. temperaturewith heat for 20 hours
  3. customAfter the completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. extractionextracted with ethyl acetate (10 ml×2)
  6. washThe organic phase was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-c10940e19ee44849a4fdc6bae3e7e73d
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

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