Reaction #2460320

Reaction equation

water

sodium hydroxide

tetraethyl p-xylylenebisphosphonate

4-bromobenzaldehyde

→

E,E-1,4-Bis(p-bromostyryl)benzene

Solvents

benzene

Conditions

Workup

1. 1
   Temperaturethe mixture was refluxed under nitrogen for 1 hour
2. 2
   Temperatureto cool
3. 3
   OtherA yellow solid was collected
4. 4
   Washwashed three times with water, methanol and ether
5. 5
   OtherThe product was purified by recrystallization from xylenes
6. 6
   Otherwas isolated in 61.9% (1.73 g)
7. 7
   Otheryield (Product is insoluble in standard solvents)

Procedure

50% aqueous sodium hydroxide (20 ml) was added to a solution of tetraethyl p-xylylenebisphosphonate (2.40 g, 6.35 mmol) (25) and 4-bromobenzaldehyde (2.41 g, 13.02 mmol) in 10 ml of benzene. Tetra-n-butylammonium iodide (148 mmg) was added and the mixture was refluxed under nitrogen for 1 hour. The reaction mixture was allowed to cool and diluted by the addition of water (25 ml). A yellow solid was collected and washed three times with water, methanol and ether. The product was purified by recrystallization from xylenes and was isolated in 61.9% (1.73 g) yield (Product is insoluble in standard solvents).

Source