Triethyl phosphite → Phosphonic acid, P,P'-(1,4-phenylenebis(methylene))bis-, P,P,P',P'-tetraethyl ester

HRID 2222748

Reaktionsgleichung

Reaktionsgleichung von HRID 2222748
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Br)=[CH:5][CH:4]=1.[P:11]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])[O:12]CC>>[C:6]1([CH2:9][P:11](=[O:12])([O:15][CH2:16][CH3:17])[O:18][CH2:19][CH3:20])[CH:7]=[CH:8][C:3]([CH2:2][P:11](=[O:12])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])=[CH:4][CH:5]=1

Komponenten

3

Edukt 2

HCID 31215Triethyl phosphiteHCID 693351,4-Bis(bromomethyl)benzene

Produkt 1

HCID 78303Phosphonic acid, P,P'-(1,4-phenylenebis(methylene))bis-, P,P,P',P'-tetraethyl esterAusbeute 89,1 %

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

α, α′-Dibromo-p-xylene (5.28 g, 20 mmol, 1 equiv.) and triethyl phosphite (10.3 mL, 60 mmol, 3 equiv.) were placed in a flask with a magnetic stirring bar. A distillation apparatus was attached to collect ethyl bromide formed along with the reaction. The mixture was immersed in an oil bath and heated to 130° C. for 2 h. After cooling down, white crystal crushed out and recrystalized from hexane to give the product (6.74 g, 89% yield). 1H NMR (CDCl3) δ7.24 (s, 4H), 4.00 (m, 8H), 3.12 (d, 4H, J=20.2 Hz), 1.23 (t, 12H, J=7.0 Hz).

Aufarbeitung

  1. customto collect ethyl bromide
  2. customformed along with the reaction
  3. customThe mixture was immersed in an oil bath
  4. temperatureAfter cooling down
  5. customwhite crystal crushed out and
  6. customrecrystalized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-f43118ed414e415a8a83585a3fbbb3f5
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07371887B2

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