Ammonium Chloride → HCID 86638494, Verbindung

HRID 216341

Reaktionsgleichung

Reaktionsgleichung von HRID 216341
Br[C:2]([P:5](=[O:10])([O-:9])[O:6][CH2:7][CH3:8])([F:4])[F:3].[CH:11]([Mg]Cl)(C)[CH3:12].[F:16][C:17]1[C:24]([F:25])=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=2)[CH:22]=[CH:21][C:18]=1[CH:19]=[O:20].[Cl-].[NH4+]>O1CCCC1.CC(C)=O.C(Cl)Cl>[F:16][C:17]1[C:24]([F:25])=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=2)[CH:22]=[CH:21][C:18]=1[CH:19]([OH:20])[C:2]([P:5](=[O:10])([O:9][CH2:11][CH3:12])[O:6][CH2:7][CH3:8])([F:4])[F:3]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 86638495HCID 86638495, VerbindungHCID 866384972,3-Difluoro-4-(5-fluoropyridin-2-yl)benzaldehydeHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 86638494HCID 86638494, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 21584124Propan-2-one--dichloromethane (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of ethyl bromodifluoromethylphosphonate (3.2 g, 12.1 mmol) in tetrahydrofuran (20 mL) was added dropwise to a solution of isopropylmagnesium chloride (2 M in tetrahydrofuran) (6.1 mL, 12.1 mmol) in tetrahydrofuran (20 mL) at −78° C. After stirring at −78° C. for 5 min, a solution of 2,3-difluoro-4-(5-fluoropyridin-2-yl)benzaldehyde (1.92 g, 8.1 mmol) in tetrahydrofuran (20 mL) was added dropwise. After stirring for a further 5 min at −78° C. then a further 1 h between −78 and 0 then a further 1 h between 0 and ambient temperature. The reaction mixture was poured into saturated ammonium chloride and extracted with methylene chloride. Combined extracts were washed with saturated aqueous sodium bicarbonate, dried (sodium sulfate) and concentrated in vacuo to afford a slightly yellow oil. Chromatography over silica eluting with 0-40% acetone/methylene chloride afforded diethyl {2-[2,3-difluoro-4-(5-fluoropyridin-2-yl)phenyl]-1,1-difluoro-2-hydroxyethyl}phosphonate as an off-white solid.

Aufarbeitung

  1. stirringAfter stirring for a further 5 min at −78° C.
  2. customa further 1 h
  3. customa further 1 h between 0 and ambient temperature
  4. extractionextracted with methylene chloride
  5. washCombined extracts were washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customto afford a slightly yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-0c6c457868c742259cdaa7875a2be4f2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193228B2

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