Réaction #7291

Équation de réaction

4-bromobenzaldehyde

4-bromobenzylbromide

triethylphosphite

sodium hydride

→

desired product

Rendement 65.0%

4,4′-dibromostilbene

Rendement 65.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Autreequipped with a stirrer
2. 2
   workup.ADDITIONThe temperature was dropped to room temperature
3. 3
   AutreAfter an ice bath was installed
4. 4
   workup.STIRRINGthe resultant was stirred for 30 minutes
5. 5
   Autreice bath was removed
6. 6
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 12 hours
7. 7
   workup.ADDITIONThe reaction mixture was poured into cold water
8. 8
   Autreto give solid
9. 9
   FiltrationThis solid was filtered
10. 10
    Lavagethoroughly washed with water and methanol
11. 11
    Autredried
12. 12
    Autrerecrystallized
13. 13
    Autreto obtain white crystal, which
14. 14
    Autrewas sufficiently dried in a vacuum oven at 40° C.

Mode opératoire

47 g (0.188 mol) of 4-bromobenzylbromide and 37.5 g (0.224 mol) of check triethylphosphite were put into a 500 ml 3-neck round-bottom flask equipped with a stirrer, a thermometer and a reflux condenser under an argon atmosphere, and the resulting mixture was stirred at 150° C. for 4 hours. The temperature was dropped to room temperature, and 250 ml of anhydrous DMF was added. After an ice bath was installed, 11.28 g (0.282 mol) of sodium hydride (60%) was slowly added and the resultant was stirred for 30 minutes. After 33.7 g (0.182 mol) of 4-bromobenzaldehyde was slowly added, ice bath was removed, and then the reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into cold water to give solid. This solid was filtered, thoroughly washed with water and methanol, dried and then recrystallized, to obtain white crystal, which was sufficiently dried in a vacuum oven at 40° C. to give 40 g (yield: 63%) of the desired product, and its melting point was 212° C.–213° C.

Source