Triethyl phosphite → Diethyl 4-cyano-2-fluorobenzylphosphonate

HRID 1766951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766951
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[F:11].[P:12]([O:19]CC)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH2:2][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])=[C:4]([F:11])[CH:5]=1)#[N:8]

Komponenten

3

Edukt 2

HCID 31215Triethyl phosphiteHCID 27831494-(Bromomethyl)-3-fluorobenzonitrile

Produkt 1

HCID 10967607Diethyl 4-cyano-2-fluorobenzylphosphonateAusbeute 103,8 %

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 4-(bromomethyl)-3-fluorobenzonitrile (1.5 g, 7.0 mmol)[J. Med. Chem., 40, 2064 (1997)] and triethyl phosphite (1.4 g, 8.4 mmol) was heated at 150° C. for 2 hours. At the end of this time, the reaction mixture was concentrated under reduced pressure. Volatile materials in the residue thus obtained were removed by heating said residue at 100° C. in vacuo for 1 hour to afford the title compound (1.97 g, quantitative yield) as an oil which solidified in the freezer. This oily product was used in the next step without further purification.

Aufarbeitung

  1. concentrationAt the end of this time, the reaction mixture was concentrated under reduced pressure
  2. customVolatile materials in the residue thus obtained
  3. customwere removed
  4. temperatureby heating
  5. customat 100° C.
  6. customfor 1 hour

Quellen und Nachweise

ORD-Eintrag
ord-412b288457da462598dc9fcd676f9657
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230023B2

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