Ammonium Chloride → 5-(2,6-Difluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidine

HRID 474689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474689
[CH3:1]C([O-])(C)C.[K+].[F:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([F:27])[C:15]=1[O:16][C:17]1[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[N:21][CH:22]=1)[CH:11]=O.[NH4+].[Cl-]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[F:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH2:1])[CH:13]=[C:14]([F:27])[C:15]=1[O:16][C:17]1[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[N:21][CH:22]=1

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 866662153,5-Difluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)benzaldehyde

Produkt 1

HCID 677743945-(2,6-Difluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidineAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred suspension of methyltriphenylphosphonium bromide (3.85 g, 10.77 mmol) and KOt-Bu (1.309 g, 11.67 mmol) in dry THF (50 mL), which was stirred at room temperature for 1 h under nitrogen, was added 3,5-difluoro-4((2-(trifluoromethyl) pyrimidin-5-yl)oxy)benzaldehyde (2.73 g, 8.98 mmol). The mixture was stirred at room temperature for 3 h. The reaction mixture was neutrilized with sat. NH4Cl. The aqueous phase was extracted with EA. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification via flash chromatography afforded the title compound (1.47 g, 4.86 mmol, 54.2% yield) as a yellow oil. LCMS: rt=3.72 min, [M+H+]=303

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. extractionThe aqueous phase was extracted with EA
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-87f36b816d354c569af878fef1c4eb1b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637536B2

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