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Water → (E)-1,2-difluoro-1-(4-propylphenyl)ethylene

HRID 37023
Notes
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Reaction equation

HRID 37023 reaction equation
[F:1]/[C:2](/[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)=[C:3](/[F:8])\[Si](C)(C)C.[F-].[K+].O>C(#N)C>[F:1]/[C:2](/[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)=[CH:3]/[F:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962Water2×HCID 522689Potassium FluorideHCID 19934212HCID 19934212, compound

Product 1

HCID 67780891(E)-1,2-difluoro-1-(4-propylphenyl)ethyleneYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Then, 19.1 g (0.075 mol) of the obtained (Z)-1,2-difluoro-1-(4-n-propylphenyl)-2-trimethylsilylethylene was dissolved in 50 ml of acetonitrile, and then 8.70 g (0.15 mol) of potassium fluoride and 4.05 g (0.225 mol) of water were added thereto. The mixture was reacted for one hour at 70° C. The reaction mixture was cooled, and then 200 ml of water was added thereto. The mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over CaCl2. After filtration, the solvent and low boiling substances were distilled off, and the residue was further distilled under reduced pressure to obtain 11.3 g (yield: 83%) of (E)-1,2-difluoro-1-(4-propylphenyl)ethylene.

Workup

  1. customThe mixture was reacted for one hour at 70° C
  2. temperatureThe reaction mixture was cooled
  3. extractionThe mixture was extracted with methylene chloride
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over CaCl2
  6. filtrationAfter filtration
  7. distillationthe solvent and low boiling substances were distilled off
  8. distillationthe residue was further distilled under reduced pressure

Sources & evidence

ORD record
ord-6abe231905dc4727a9662231775d9c62
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05419851

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes