Triethyl phosphite → Diethyl 3-chloro-4-nitrobenzylphosphonate

HRID 515310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515310
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([Cl:12])[CH:4]=1.[P:13]([O:20]CC)([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16]>>[Cl:12][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[N+:9]([O-:11])=[O:10])[CH2:2][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16]

Komponenten

3

Edukt 2

HCID 31215Triethyl phosphiteHCID 671933714-(Bromomethyl)-2-chloro-1-nitrobenzene

Produkt 1

HCID 86654007Diethyl 3-chloro-4-nitrobenzylphosphonateAusbeute 48 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-(Bromomethyl)-2-chloro-1-nitrobenzene (17.21 mmol, 4.31 g) and triethyl phosphite (25.8 mmol, 4.34 mL, 4.29 g) were combined and heated to 100° C. for 4 hours. The reaction mixture was quenched with water and extracted into ether. The organic phase was concentrated under vacuum. The resulting residue was purified by silica chromatography (eluting with dichloromethane-2% dichloromethane/methanol) to give the intermediate diethyl 3-chloro-4-nitrobenzylphosphonate (2.54 g).

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionextracted into ether
  3. concentrationThe organic phase was concentrated under vacuum
  4. customThe resulting residue was purified by silica chromatography (eluting with dichloromethane-2% dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-6ea87df4ba9246f685f279b775a66560
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108939B2

Notizen zur Reaktion

Wird geladen…