Phenol → 4,5-Difluoro-6-phenoxypyrimidine

HRID 1857966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1857966
CC(C)([O-])C.[K+].[C:7]1([OH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1([O-])C=CC=CC=1.[K+].[F:22][C:23]1[C:28]([F:29])=[C:27](F)[N:26]=[CH:25][N:24]=1>C1COCC1>[F:29][C:28]1[C:27]([O:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:26][CH:25]=[N:24][C:23]=1[F:22]

Komponenten

6

Edukt 4

HCID 996PhenolHCID 35727644,5,6-TrifluoropyrimidineHCID 23665647Potassium tert-butoxideHCID 23670670Potassium phenoxide

Produkt 1

HCID 158696744,5-Difluoro-6-phenoxypyrimidineAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

With stirring, 50.4 g (0.45 mol) of potassium tert-butoxide (M=112.22) are added to a solution of 42.4 g (0.45 mol) of phenol in 400 ml of THF. The resulting potassium phenolate solution is added dropwise to a solution of 80 g (0.6 mol) of 4,5,6-trifluoropyrimidine in 1 l of THF which had been cooled to 0° C., and the mixture is stirred for 30 minutes. The solution is concentrated under reduced pressure and the residue is mixed with water and extracted with ethyl acetate. The organic phase is separated off, dried over sodium sulphate and concentrated under reduced pressure. The crude product is stirred with petroleum ether and filtered off. 63.8 g (68.1% of theory) of 5,6-difluoro-4-phenoxypyrimidine of melting point 65-66° C. are obtained.

Aufarbeitung

  1. stirringthe mixture is stirred for 30 minutes
  2. concentrationThe solution is concentrated under reduced pressure
  3. additionthe residue is mixed with water
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is separated off
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. stirringThe crude product is stirred with petroleum ether
  9. filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag
ord-c9ac4c0cdb5144079daf4b6d32e6173c
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06150374

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