反応 #7291

反応方程式

4-bromobenzaldehyde

4-bromobenzylbromide

triethylphosphite

sodium hydride

→

desired product

収率 65.0%

4,4′-dibromostilbene

収率 65.0%

溶媒

DMF

反応条件

後処理

1. 1
   その他equipped with a stirrer
2. 2
   workup.ADDITIONThe temperature was dropped to room temperature
3. 3
   その他After an ice bath was installed
4. 4
   workup.STIRRINGthe resultant was stirred for 30 minutes
5. 5
   その他ice 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
   その他to give solid
9. 9
   ろ過This solid was filtered
10. 10
    洗浄thoroughly washed with water and methanol
11. 11
    その他dried
12. 12
    その他recrystallized
13. 13
    その他to obtain white crystal, which
14. 14
    その他was sufficiently dried in a vacuum oven at 40° C.

実験手順

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.

出典