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Sodium hydride → 4,4'-Dibromostilbene

HRID 7195
ノート
印刷プレビュー

反応式

HRID 7195 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C(OP(OCC)OCC)C.[H-].[Na+].[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:27][C:26]2[CH:29]=[CH:30][C:23]([Br:22])=[CH:24][CH:25]=2)=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 31215Triethyl phosphiteHCID 685274-Bromobenzyl bromideHCID 707414-Bromobenzaldehyde

生成物 1

HCID 533959814,4'-Dibromostilbene収率 65%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °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.

後処理

  1. customequipped with a stirrer
  2. additionThe temperature was dropped to room temperature
  3. customAfter an ice bath was installed
  4. stirringthe resultant was stirred for 30 minutes
  5. customice bath was removed
  6. stirringthe reaction mixture was stirred at room temperature for 12 hours
  7. additionThe reaction mixture was poured into cold water
  8. customto give solid
  9. filtrationThis solid was filtered
  10. washthoroughly washed with water and methanol
  11. customdried
  12. customrecrystallized
  13. customto obtain white crystal, which
  14. customwas sufficiently dried in a vacuum oven at 40° C.

出典と根拠

ORDレコード
ord-f7c613e5037143f2acbfe849c8d77347
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07084231B2

反応ノート

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