Water → 4,5-Difluoro-6-phenoxypyrimidine

HRID 1871517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1871517
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[F:14][C:15]1[C:20]([F:21])=[C:19](F)[N:18]=[CH:17][N:16]=1.O>O1CCCC1>[O:7]([C:19]1[C:20]([F:21])=[C:15]([F:14])[N:16]=[CH:17][N:18]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 996PhenolHCID 35727644,5,6-TrifluoropyrimidineHCID 23665647Potassium tert-butoxide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 42.4 g (0.45 mol) of phenol and 50.4 g (0.45 mol) of potassium tert-butoxide in 400 ml of tetrahydrofuran is added dropwise at 0° C. to a solution of 80 g (0.6 mol) of 4,5,6-trifluoropyrimidine in 1 l of tetrahydrofuran. When the addition was complete, the reaction mixture was stirred for 30 minutes at 0° C. and then poured into water and extracted using ethyl acetate. The organic phase is dried over sodium sulphate and concentrated in vacuo, and the residue is stirred with low-boiling petroleum ether. 63.8 g (68.1% of theory) of 4-phenoxy-5,6-difluoropyrimidine of melting point 65-66° C. are obtained.

Aufarbeitung

  1. additionWhen the addition
  2. extractionextracted
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. stirringthe residue is stirred with low-boiling petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-04e217c78e284c6b86f5f1bd59df6a57
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06103717

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