Reacción #2460324

Ecuación de reacción

2-bromo-α,α′-dibromo-p-xylene

triethyl phosphite

→

tetraethyl 2-bromo-p-xylenebisphosphonate

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe excess triethyl phosphite was removed under reduced pressure, 60 ml of hexanes
2. 2
   workup.ADDITIONwas added
3. 3
   Temperaturathe mixture was cooled at −78 ° C.
4. 4
   Otrowhite solid was formed on vigorous stirring
5. 5
   FiltraciónThe solid was collected by rapid filtration
6. 6
   Lavadowashed three times with 20 ml of cool hexanes
7. 7
   Otrodried in vacuo
8. 8
   Otroisolated in 14.0 g (72.7%)
9. 9
   Otroyield as light yellow oil

Procedimiento

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).

Fuente