Water → 4-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)benzoic acid

HRID 645299

Reaktionsgleichung

Reaktionsgleichung von HRID 645299
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:23])[CH:9]=[C:10]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)[C:11]([F:14])([F:13])[F:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.[OH2:31].[C]=O.[C:34]([OH:38])(C)(C)C>O1CCOCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:22][C:17]1[CH:16]=[C:15]([C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:34]([OH:38])=[O:31])=[CH:3][CH:4]=2)=[O:23])[CH:20]=[C:19]([Cl:21])[CH:18]=1

Komponenten

9

Edukt 5

HCID 962WaterHCID 6386tert-ButanolHCID 8471TriethylamineHCID 866264271-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-oneHCID 178418416HCID 178418416, Verbindung2×

Produkt 1

HCID 667356584-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysator2×HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 1.95 g of 1-(4-bromophenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butene-1-one that was synthesized under Synthetic Example 3 and 0.56 g of triethylamine in 10 mL of tertiary-butyl alcohol, 10 mL of dioxane, and 5 mL of water in an autoclave, 51 mg of 1,1′-bis(diphenylphosphino) ferrocene and 10 mg of palladium(II) acetate were added, the mixture was stirred for 4 hours at 110° C. in an atmosphere of carbon monoxide at 0.5 MPa followed by cooling to room temperature, and then further 10 mg of palladium(II) acetate were added, the mixture was stirred for 4 hours at 110° C. in an atmosphere of carbon monoxide at 0.5 MPa. After that, the temperature was cooled to room temperature to isolate solid matter by filtration whereto diluted hydrochloric acid was added to extract with ethyl acetate, and then an organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified using silica gel column chromatography that was eluted with ethyl acetate-hexane (1:8) to obtain 1.5 g of aimed product as resinous matter.

Aufarbeitung

  1. additionwere added
  2. temperatureAfter that, the temperature was cooled to room temperature
  3. customto isolate solid matter
  4. filtrationby filtration whereto diluted hydrochloric acid
  5. additionwas added
  6. extractionto extract with ethyl acetate
  7. dry with materialan organic layer was dried with anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting residue was purified
  10. washwas eluted with ethyl acetate-hexane (1:8)

Quellen und Nachweise

ORD-Eintrag
ord-f060f149bc974205932adc4af2078553
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700808B2

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