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1,2-Dichloroethane → 1-(4-Chloro-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one

HRID 1848311
Notes
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Reaction equation

HRID 1848311 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[O:9])[CH:5]=[CH:4][C:3]=1[Cl:11].[Cl:12][C:13]1[CH:14]=[C:15]([C:20](=O)[C:21]([F:24])([F:23])[F:22])[CH:16]=[C:17]([Cl:19])[CH:18]=1.ClCCCl.C(=O)([O-])[O-].[K+].[K+]>C(N(CC)CC)C>[Cl:11][C:3]1[CH:4]=[CH:5][C:6]([C:8](=[O:9])[CH:10]=[C:20]([C:15]2[CH:16]=[C:17]([Cl:19])[CH:18]=[C:13]([Cl:12])[CH:14]=2)[C:21]([F:24])([F:23])[F:22])=[CH:7][C:2]=1[CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 11430Potassium CarbonateHCID 5927434'-Chloro-3'-methylacetophenoneHCID 27582311-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 750457831-(4-Chloro-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-oneYield 88.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

3.0 g of 4-chloro-3-methylacetophenone, 4.35 g of 3′,5′-dichloro-2,2,2-trifluoroacetophenone, 30 ml of 1,2-dichloroethane, 2.46 g of potassium carbonate and 0.18 g of triethylamine were fed and the mixture was refluxed by heating for 16 hours. The reaction solution was cooled to room temperature, and separated by adding 200 ml of ethyl acetate and iced water. The organic phase was washed with diluted hydrochloric acid and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent is a mixed liquid of hexane:ethyl acetate=9:1) to obtain 6.2 g of 1-(4-chloro-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one as brown liquid.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 16 hours
  3. customseparated
  4. additionby adding 200 ml of ethyl acetate and iced water
  5. washThe organic phase was washed with diluted hydrochloric acid and saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-66c4e54915904ab2815142152d2ade37
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952175B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes