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Sodium hydride → 4,4'-Dibromostilbene

HRID 7195
Notes
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Reaction equation

HRID 7195 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 533959814,4'-DibromostilbeneYield 65%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
150 °C

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-f7c613e5037143f2acbfe849c8d77347
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07084231B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes