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

HRID 1848314

Reaktionsgleichung

Reaktionsgleichung von HRID 1848314
C([OH:5])(C)(C)C.[O:6]1[CH2:11][CH2:10]OCC1.BrC1[CH:18]=[CH:17][C:16]([C:19](=[O:34])[CH:20]=[C:21]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)[C:22]([F:25])([F:24])[F:23])=[CH:15][CH:14]=1.[C]=O>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.C(N(CC)CC)C.O>[Cl:33][C:28]1[CH:27]=[C:26]([C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][C:19]([C:16]2[CH:17]=[CH:18][C:10]([C:11]([OH:6])=[O:5])=[CH:14][CH:15]=2)=[O:34])[CH:31]=[C:30]([Cl:32])[CH:29]=1

Komponenten

9

Edukt 4

HCID 6386tert-ButanolHCID 312751,4-DioxaneHCID 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 4

HCID 167845palladium(II) acetateKatalysator2×HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

After adding 51 mg of 1,1′-bis(diphenylphosphino)ferrocene and 10 mg of palladium (II) acetate to tertiary-butyl alcohol (10 ml), dioxane (10 ml) and water (5 ml) solution of 1.95 g of 1-(4-bromophenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one which was synthesized in accordance with Synthesis Example of Raw Material 5, and 0.56 g of triethylamine in an autoclave, and stirring for 4 hours at 110° C. under 0.5 MPa of carbon monoxide atmosphere, the mixture was left to cool to room temperature. 10 mg of palladium (II) acetate was further added and the mixture was stirred for 4 hours at 110° C. under 0.5 MPa of carbon monoxide atmosphere. Then, the mixture was left to cool to room temperature, and the solid was filtered. Diluted hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography which eluted the residue with ethyl acetate-hexane (1:8), to obtain 1.56 g of the target product as a resinous solid.

Aufarbeitung

  1. waitthe mixture was left
  2. waitThen, the mixture was left
  3. temperatureto cool to room temperature
  4. filtrationthe solid was filtered
  5. additionDiluted hydrochloric acid was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography which
  10. washeluted the residue with ethyl acetate-hexane (1:8)

Quellen und Nachweise

ORD-Eintrag
ord-02fb65894c534c49a6c89ac5ca09653a
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952175B2

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