5-Chloro-2-(difluoromethoxy)benzaldehyd → HCID 86721086, Verbindung

HRID 1396308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1396308
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]([F:13])[F:12])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH:14]([Mg]Br)=[CH2:15]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]([F:12])[F:13])=[C:6]([CH:7]([OH:8])[CH:14]=[CH2:15])[CH:9]=1

Komponenten

4

Edukt 2

HCID 47709495-Chloro-2-(difluoromethoxy)benzaldehydHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 86721086HCID 86721086, VerbindungAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

5-Chloro-2-(difluoromethoxy)benzaldehyde (0.480 g, 2.324 mmol) was dissolved in dry THF (11.62 mL) and the reaction was cooled to −78° C. under argon. Vinyl magnesium bromide (3.49 mL, 3.49 mmol) was then added dropwise. After the reaction was complete, the ice bath was removed and reaction was allowed to warm to rt and stirred for an additional 2 h. The reaction was cooled to 0° C. and then carefully quenched with saturated ammonium chloride. The mixture was then diluted with water and extracted with EtOAc (3×). The combined organic phases were dried over Na2SO4, filtered and concentrated to yield 1-(5-chloro-2-(difluoromethoxy)phenyl)prop-2-en-1-ol (561 mg, 103%) as a clear oil. MS (ESI) m/z: 236.9 (M+H, Chlorine isotope peak)+.

Aufarbeitung

  1. customthe ice bath was removed
  2. customreaction
  3. temperatureto warm to rt
  4. temperatureThe reaction was cooled to 0° C.
  5. customcarefully quenched with saturated ammonium chloride
  6. additionThe mixture was then diluted with water
  7. extractionextracted with EtOAc (3×)
  8. dry with materialThe combined organic phases were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3ad229c87ba9493ca16a142808fb960a
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901115B2

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