Trifluoroacetic acid → Methyl 4-(1-carboxycyclopropyl)-2,3,5,6-tetrafluorobenzoate

HRID 981267Notes

Reaction equation

HRID 981267 reaction equation
C1(C(C2C=CC=CC=2)[O:8][C:9]([C:11]2([C:14]3[C:23]([F:24])=[C:22]([F:25])[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([F:26])[C:15]=3[F:27])[CH2:13][CH2:12]2)=[O:10])C=CC=CC=1.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[C:9]([C:11]1([C:14]2[C:15]([F:27])=[C:16]([F:26])[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:22]([F:25])[C:23]=2[F:24])[CH2:13][CH2:12]1)([OH:10])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15136256Methyl 4-(1-diphenylmethoxycarbonylcyclopropyl)-2,3,5,6-tetrafluorobenzoate

Product 1

HCID 15136257Methyl 4-(1-carboxycyclopropyl)-2,3,5,6-tetrafluorobenzoateYield 88.8%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

In 60 ml of anisole was dissolved 22.5 g of methyl 4-(1-diphenylmethoxycarbonylcyclopropyl)-2,3,5,6tetrafluorobenzoate. To the resulting solution was added 80 ml of trifluoroacetic acid. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. n-Hexane was added to the residue obtained. The resulting crystals were collected by filtration to obtain 12.7 g (yield: 88.8%) of methyl 4-(1-carboxycyclopropyl)-2,3,5,6tetrafluorobenzoate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionn-Hexane was added to the residue
  3. customobtained
  4. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-1da36ee1ab2d40cab612beee20b47c58
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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