Triethyl phosphite → HCID 86600084, compound

HRID 2373142Notes

Reaction equation

HRID 2373142 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]Br)[CH:5]=[CH:4][C:3]=1[CH2:10]Br.[P:12]([O:19][CH2:20][CH3:21])([O:16]CC)[O:13][CH2:14][CH3:15]>>[Br:1][C:2]1([P:12]([O:13][CH2:14][CH3:15])(=[O:16])[O:19][CH2:20][CH3:21])[C:7]([P:12]([O:19][CH2:20][CH3:21])(=[O:16])[O:13][CH2:14][CH3:15])=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]1[CH3:10]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 2622392-Bromo-1,4-bis(bromomethyl)benzene

Product 1

HCID 86600084HCID 86600084, compound

Conditions

Temperature
180 °C

Procedure

The mixture of 2-bromo-α,α′-dibromo-p-xylene (68) (14.43 g, 0.042 mol) and triethyl phosphite (145 ml) was refluxed at 180° C. overnight. The excess triethyl phosphite was removed under reduced pressure, 60 ml of hexanes was added, the mixture was cooled at −78 ° C. and white solid was formed on vigorous stirring. The solid was collected by rapid filtration, washed three times with 20 ml of cool hexanes, dried in vacuo and isolated in 14.0 g (72.7%) yield as light yellow oil.1H NMR (CDCl3, 500 MHz) δppm: 7.51 (s, br, 1H), 7.40 (dd, 3J=7.7 Hz, 4J=2.2 Hz, 1H), 7.21 (d, 3J=8.0 Hz, 1H) 4.04 (m, 8H, CH2), 3.38 (d, J=21.5 Hz, 2H, CH2), 3.09 (d, J=21.5 Hz, 2H, CH2), 1.25 (m, 12H, CH3).

Workup

  1. customThe excess triethyl phosphite was removed under reduced pressure, 60 ml of hexanes
  2. additionwas added
  3. temperaturethe mixture was cooled at −78 ° C.
  4. customwhite solid was formed on vigorous stirring
  5. filtrationThe solid was collected by rapid filtration
  6. washwashed three times with 20 ml of cool hexanes
  7. customdried in vacuo
  8. customisolated in 14.0 g (72.7%)
  9. customyield as light yellow oil

Sources & evidence

ORD record
ord-339d2199b5f14f5fbd5f02d30674ce67
Source dataset
uspto-grants-2008_12
Patent number
US07459106B2

Reaction notes

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