Tetrahydrofuran → 5-(2-Fluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidine

HRID 474685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474685
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][CH:16]=1)[CH:5]=O.[H-].[Na+].[CH2:23]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH2:23])[CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 866662143-Fluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)benzaldehyde

Produkt 1

HCID 677766905-(2-Fluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidineAusbeute 27,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 74505Methyltriphenyliphosphonium bromideKatalysator

Versuchsvorschrift

To a stirred suspension of 3-fluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)benzaldehyde (2 g, 6.99 mmol) and methyltriphenylphosphonium bromide (2.496 g, 6.99 mmol) in dry THF (40 mL) was added NaH (0.978 g, 24.46 mmol) under nitrogen at 0° C. The mixture was stirred at room temperature for 4 h. The organic layer was washed three times with brine, dried over Na2SO4, filtered, and concentrated. Purification via flash chromatography afforded the title compound (540 mg, 1.900 mmol, 27.2% yield). LCMS: rt=3.65 min, [M+H+]=285

Aufarbeitung

  1. washThe organic layer was washed three times with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2183919669b74a2192a30435a2abf4bc
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637536B2

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