Dicyclohexylcarbodiimide → 2,3,4,5,6-Pentafluorophenyl 4-ethenylbenzoate

HRID 2116434Notes

Reaction equation

HRID 2116434 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[F:12][C:13]1[C:18](O)=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[C:14]=1[F:23].C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.O1CCCC1>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][C:18]2[C:17]([F:20])=[C:16]([F:21])[C:15]([F:22])=[C:14]([F:23])[C:13]=2[F:12])=[O:8])=[CH:5][CH:4]=1)=[CH2:2]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 140984-Vinylbenzoic acid

Product 1

HCID 586255842,3,4,5,6-Pentafluorophenyl 4-ethenylbenzoateYield 93.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a mixture solvent of 500 mL of ethyl acetate and 150 mL of tetrahydrofuran were dissolved 50 g of 4-vinylbenzoic acid and 62.1 g of pentafluorophenol, and the solution was ice-cooled. To the solution was added 69.65 g of dicyclohexylcarbodiimide, and the mixture was stirred under ice-cooling for 1 hour and then at room temperature for 1 hour. Precipitated dicyclohexylurea was filtered off and the filtrate was concentrated under a reduced pressure. To the residue was added 150 mL of hexane, and precipitated dicyclohexylurea was filtered off. Then, the filtrate was concentrated under a reduced pressure to give 99 g of pentafluorophenyl 4-vinylbenzoate.

Workup

  1. temperaturecooled
  2. temperaturecooling for 1 hour
  3. filtrationPrecipitated dicyclohexylurea was filtered off
  4. concentrationthe filtrate was concentrated under a reduced pressure
  5. additionTo the residue was added 150 mL of hexane
  6. customprecipitated dicyclohexylurea
  7. filtrationwas filtered off
  8. concentrationThen, the filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-7fa616de18e54a1ba8b063a3fcb9d1e6
Source dataset
uspto-grants-2008_10
Patent number
US07439005B2

Reaction notes

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