Benzyl Bromide → 1-benzyl-1H-pyrrole-2-carbaldehyde

HRID 479439Notes

Reaction equation

HRID 479439 reaction equation
[H-].[Na+].[CH:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CN(C=O)C>[CH2:10]([N:6]1[CH:7]=[CH:8][CH:9]=[C:5]1[CH:3]=[O:4])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 13854Pyrrole-2-carboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 111269641-benzyl-1H-pyrrole-2-carbaldehydeYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (60% in mineral oil, 4.8 g, 120 mmol) in DMF (100 ml) was added dropwise at an ice bath temperature a solution of 2-formylpyrrole (9.5 g, 100 mmol) in DMF (10 ml). The mixture was stirred for 15 minutes at room temperature and cooled again. To the mixture was added dropwise a solution of benzylbromide (20.5 g, 120 mmol) in DMF (10 ml). The reaction mixture was stirred for 60 minutes at room temperature and poured to ice-water, and extracted with ethylacetate. The extract was washed with water and dried. The solvent was evaporated to give 1-benzyl-2-formylpyrrole (18.0 g) as an oil quantitatively.

Workup

  1. temperaturecooled again
  2. stirringThe reaction mixture was stirred for 60 minutes at room temperature
  3. extractionextracted with ethylacetate
  4. washThe extract was washed with water
  5. customdried
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2d9f1a9f7caf4e7195346325c2bc39f7
Source dataset
uspto-grants-2003_11
Patent number
US06645956B1

Reaction notes

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