Methyl 4-(1-carboxyvinyl)-2,3,5,6-tetrafluorobenzoate → Methyl 2,3,5,6-tetrafluoro-4-vinylbenzoate

HRID 981264Notes

Reaction equation

HRID 981264 reaction equation
[C:1]([C:4]([C:6]1[C:15]([F:16])=[C:14]([F:17])[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([F:18])[C:7]=1[F:19])=C)(O)=O>CN(C)C=O>[F:17][C:14]1[C:15]([F:16])=[C:6]([CH:4]=[CH2:1])[C:7]([F:19])=[C:8]([F:18])[C:9]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

3

Reactant 1

HCID 15136251Methyl 4-(1-carboxyvinyl)-2,3,5,6-tetrafluorobenzoate

Product 1

HCID 15136253Methyl 2,3,5,6-tetrafluoro-4-vinylbenzoateYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml of N,N-dimethylformamide was dissolved 3.0 g of methyl 4-(1-carboxyvinyl)-2,3,5,6-tetrafluorobenzoate. The resulting solution was stirred at 130°-140° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure. The residue obtained was purified by a column chromatography (eluant: toluene/n-hexane=1/1) to obtain 2.0 g (yield: 79.1%) of methyl 2,3,5,6-tetrafluoro-4-vinylbenzoate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue obtained
  3. customwas purified by a column chromatography (eluant: toluene/n-hexane=1/1)

Sources & evidence

ORD record
ord-d181f20a1bb94c68bb5517aa0a0adc06
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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