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

HRID 1975656
Notes
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Reaction equation

HRID 1975656 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C: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:22])C.S(=O)(=O)(O)O>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:22])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 12168182Benzene, 1-[(4-fluorophenyl)ethynyl]-4-(trifluoromethyl)-

Product 1

HCID 98172164'-Fluoro-2-(4-trifluoromethylphenyl)acetophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

To 12.2 g (46 mmol) of 4-fluoro-4'-trifluoromethyltolane, 60 ml of water, 60 ml of acetic acid, 40 ml of sulfuric acid and 13.6 g (46 mmol) of mercuric sulfate were added, and the mixture was stirred at 90° C. for 3.5 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/9) to obtain 5.1 g of 4'-fluoro-2- (4-trifluoromethylphenyl)acetophenone having a melting point of from 87° to 89° C.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with diethyl ether
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/9)

Sources & evidence

ORD record
ord-09fb09a549d346f4add477d5cea47913
Source dataset
uspto-grants-1994_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05288727

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes