Triethyl phosphite → HCID 86600083, compound

HRID 2373141Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]Br)[C:5]([Br:10])=[CH:4][C:3]=1[CH2:11]Br.[P:13]([O:20][CH2:21][CH3:22])([O:17]CC)[O:14][CH2:15][CH3:16]>>[Br:10][C:5]1([P:13]([O:14][CH2:15][CH3:16])(=[O:17])[O:20][CH2:21][CH3:22])[C:4]([P:13]([O:20][CH2:21][CH3:22])(=[O:17])[O:14][CH2:15][CH3:16])=[C:3]([CH3:11])[C:2]([Br:1])=[CH:7][CH:6]1[CH3:8]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 6402221,4-dibromo-2,5-bis(bromomethyl)benzene

Product 1

HCID 86600083HCID 86600083, compoundYield 82.2%

Conditions

Temperature: 180 °C

Procedure

The mixture of 2, 5-dibromo-α,α′-dibromo-p-xylene (67) (7.58 g, 0.018 mol) and triethyl phosphite (60 ml) was refluxed at 180° C. overnight. The excess triethyl phosphite was removed under reduced pressure, 60 ml of hexanes was added, and white solid was formed. The solid was collected by filtration, washed three times with 20 ml of hexanes and gave 7.93 g (82.2%) of product.1H NMR (CDCl3, 500 MHz) δppm: 7.62 (s, 2H, Ar—H), 4.06 (m, 8H, CH2), 3.32 (d, J=20.5 Hz, 4H, CH2), 1.28 (t, J=7.0 Hz, 12H, CH3)13C NMR (CDCl3, 125.7 MHz) δppm: 135.2, 132.5, 123.6, 62.35, 62.32, 33.4, 32.2, 16.31, 16.28GC-MS (relative intensity %): 491 (M+, <5%).

Workup

customThe excess triethyl phosphite was removed under reduced pressure, 60 ml of hexanes
additionwas added
customwhite solid was formed
filtrationThe solid was collected by filtration
washwashed three times with 20 ml of hexanes

Sources & evidence

ORD record: ord-737fcfb6b64c4e5f84d1d7fa20634013
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459106B2

Reaction notes

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