Benzyl Bromide → HCID 17221112, compound

HRID 2394390Notes

Reaction equation

HRID 2394390 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([CH:12]=[O:13])[C:6]=2[CH:5]=[CH:4]1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>CN(C)C=O>[CH2:14]([N:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([CH:12]=[O:13])[C:6]=2[CH:5]=[CH:4]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 333703Indole-4-carboxaldehyde

Product 1

HCID 17221112HCID 17221112, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (95%; 0.37 g) was suspended in 10 ml of dimethylformamide and cooled to a temperature ranging from 0° to 5° C. with stirring, under an argon gas atmosphere. To the resulting mixed liquid, there was dropwise added a solution of 2.00 g of indole-4-carbaldehyde in 5 ml of dimethylformamide over 15 minutes. After completion of the dropwise addition, the mixture was stirred at a temperature ranging from 0° to 5° C. for 30 minutes. To the reaction solution, there was added a solution of 2.47 g of benzyl bromide in 5 ml of dimethylformamide, followed by stirring at room temperature for 2 hours. The reaction solution was poured into 200 ml of a 10% ammonium chloride aqueous solution, followed by extraction with ethyl acetate (200 ml×2). After washing the extract with a saturated common salt solution, it was dried over anhydrous sodium sulfate, followed by evaporation of the solvent under reduced pressure to give 3.18 g of 1-benzylindole-4-carbaldehyde as brown crystals. The yield thereof was found to be 98%.

Workup

  1. temperaturecooled to a temperature
  2. customranging from 0° to 5° C.
  3. additionTo the resulting mixed liquid, there
  4. additionAfter completion of the dropwise addition
  5. stirringthe mixture was stirred at a temperature
  6. stirringby stirring at room temperature for 2 hours
  7. extractionfollowed by extraction with ethyl acetate (200 ml×2)
  8. washAfter washing the
  9. extractionextract with a saturated common salt solution, it
  10. dry with materialwas dried over anhydrous sodium sulfate
  11. customfollowed by evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-3cbbecf3382340c2b98c8feca6d94b84
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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