3-(Trifluoromethyl)phenol → 4-(3-Trifluoromethylphenoxy)-2-(4-Trifluoromethylphenyl)-Pyrimidine

HRID 411827

Reaktionsgleichung

Reaktionsgleichung von HRID 411827
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Cl[C:13](Cl)=[CH:14][CH:15]=O.C([O-])(=O)C.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[NH2+:29])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][C:15]1[CH:14]=[CH:13][N:30]=[C:28]([C:27]2[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:33])[F:34])=[CH:32][CH:31]=2)[N:29]=1

Komponenten

6

Edukt 4

HCID 73763-(Trifluoromethyl)phenolHCID 10340Sodium CarbonateHCID 175543,3-Dichloro-2-propenalHCID 185417004-Trifluoromethylbenzamidinium acetate

Produkt 1

HCID 99299504-(3-Trifluoromethylphenoxy)-2-(4-Trifluoromethylphenyl)-PyrimidineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-Trifluoromethylphenol (5 mmoles) and subsequently 3,3-dichloroacrolein (5 mmoles) are added to a mixture consisting of a 4-trifluoromethylbenzamidinium acetate (5 mmoles), sodium carbonate (40 mmoles) and acetonitril (35 ml), which is stirred under reilux. The reaction mixture is stirred for 20 hours under reflux and subsequently cooled down to ambient temperature and filtered through silica. The organic phase is washed with ethyl acetate and concentrated in vacuo. The residue is purified by chromatography on Al2O3 (petrol ethers/ethyl acetate: 2/1) to yield 1.1 g (60%) of the pure product having a melting point of 66-67° C.

Aufarbeitung

  1. stirringThe reaction mixture is stirred for 20 hours
  2. temperatureunder reflux
  3. filtrationfiltered through silica
  4. washThe organic phase is washed with ethyl acetate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by chromatography on Al2O3 (petrol ethers/ethyl acetate: 2/1)

Quellen und Nachweise

ORD-Eintrag
ord-a0b0745c9fb7486b9339e07a4d005f05
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559307B2

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