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

HRID 2222748

Reaction equation

HRID 2222748 reaction equation
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

Participants

3

Reactant 2

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

Product 1

HCID 78303Phosphonic acid, P,P'-(1,4-phenylenebis(methylene))bis-, P,P,P',P'-tetraethyl esterYield 89.1%

Conditions

Temperature
130 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f43118ed414e415a8a83585a3fbbb3f5
Source dataset
uspto-grants-2008_05
Patent number
US07371887B2

Linked notes

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