Reaction #2460323

Reaction equation

2, 5-dibromo-α,α′-dibromo-p-xylene

2,5-dibromo-α,α′-dibromo-p-xylene

triethyl phosphite

→

product

Yield 82.2%

tetraethyl 2,5-dibromo-p-xylenebisphosphonate

Yield 82.2%

Conditions

Workup

1. 1
   OtherThe excess triethyl phosphite was removed under reduced pressure, 60 ml of hexanes
2. 2
   workup.ADDITIONwas added
3. 3
   Otherwhite solid was formed
4. 4
   FiltrationThe solid was collected by filtration
5. 5
   Washwashed three times with 20 ml of hexanes

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%).

Source