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Acetic Acid → 4'-Fluoro-2-(4-trifluoromethylphenyl)acetophenone

HRID 968076
Notes
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Reaction equation

HRID 968076 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](N(C)C)=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(O)(=[O:25])C.Cl>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 697465101-(4-fluorophenyl)-2-(4-trifluoromethylphenyl)-N,N-dimethylethenylamine

Product 1

HCID 98172164'-Fluoro-2-(4-trifluoromethylphenyl)acetophenoneYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 200 ml four-necked flask equipped with a thermometer, a stirrer and a reflux condenser, 15.5 g (50 mmol) of 1-(4-fluorophenyl)-2-(4-trifluoromethylphenyl)-N,N-dimethylethenylamine, 80 ml of acetic acid and 30 ml of concentrated hydrochloric acid were charged and reacted with stirring for two hours under refluxing under heating by an oil bath. After completion of reaction, 500 ml of water was added, and precipitated crystals were collected by filtration and washed with a 2% sodium hydrogen carbonate aqueous solution and water. Then, the crystals were further washed and purified with 20 ml of n-hexane and then vacuum-dried to obtain 12.7 g (yield: 90.3%) of the desired compound (melting point: 93-95° C.) as slightly yellow crystals.

Workup

  1. additionwere charged
  2. customreacted
  3. temperatureunder refluxing
  4. temperatureunder heating by an oil bath
  5. additionwas added
  6. customprecipitated crystals
  7. filtrationwere collected by filtration
  8. washwashed with a 2% sodium hydrogen carbonate aqueous solution and water
  9. washThen, the crystals were further washed
  10. custompurified with 20 ml of n-hexane
  11. customvacuum-dried

Sources & evidence

ORD record
ord-d32059cc5c3346b889444bdb232ea8aa
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06956132B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes