Sodium Iodide → Diethyl 2-(trifluoromethyl)benzylphosphonate

HRID 736039

Reaktionsgleichung

Reaktionsgleichung von HRID 736039
[I-].[Na+].Cl[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([F:14])([F:13])[F:12].[P:15]([O:22]CC)([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18]>C(#N)C>[CH2:17]([O:16][P:15]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([F:14])([F:13])[F:12])(=[O:22])[O:19][CH2:20][CH3:21])[CH3:18]

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 31215Triethyl phosphite2×HCID 890281-(Chloromethyl)-2-(trifluoromethyl)benzene

Produkt 1

HCID 15818095Diethyl 2-(trifluoromethyl)benzylphosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a suspension of sodium iodide (3.85 g, 25.6 mmol, 1 equiv.) in acetonitrile at room temperature under argon is added neat 1-chloromethyl-2-trifluoromethyl-benzene (commercially available from Acros Organics USA). To the resulting milky suspension is added freshly distilled triethyl phosphite (4.26 g, 25.6 mmol, 1 equiv.) and the resulting solution is stirred overnight at room temperature. After that time further triethyl phosphite (2.13 g, 12.9 mmol, 0.5 equiv.) is added and the reaction mixture heated at reflux for 1 hour. After cooling down to room temperature all volatiles were evaporated under reduced pressure. The residue is taken-up in dichloromethane and filtered through paper and the filtrate is concentrated under reduced pressure to yield the desired material as a clear oil pure enough to be used in the following step without further purification (7.46 g, 98%).

Aufarbeitung

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 1 hour
  3. temperatureAfter cooling down to room temperature all volatiles
  4. customwere evaporated under reduced pressure
  5. filtrationfiltered through paper
  6. concentrationthe filtrate is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-866ca2e02fe7473f80b86807ac5b81a6
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595315B2

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