N-bromobutanimide → 1H-Pyrrole-2-carbonitrile, 1-[4-(bromomethyl)phenyl]-

HRID 274566

Reaction equation

HRID 274566 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]#[N:14])=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C1C(C(OO)=O)=CC=CC=1>[Br:15][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]#[N:14])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27977151-(4-Methylphenyl)pyrrole-2-carbonitrile

Product 1

HCID 103328611H-Pyrrole-2-carbonitrile, 1-[4-(bromomethyl)phenyl]-Yield 94%

Reagents, catalysts & solvents 2

HCID 523077Perbenzoic acidCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 1-(4-methylphenyl)pyrrole-2-carbonitrile (4.9 g), N-bromosuccinimide (5.5 g) and perbenzoic acid (65 mg) in carbon tetrachloride was heated under reflux in light radiation for 2 hours. After removal of insoluble materials by filtration, the filtrate was concentrated to dryness. The residue was purified by column chromatography on silica gel to afford a colorless syrup (6.6 g, 93%).

Workup

  1. temperatureunder reflux in light radiation for 2 hours
  2. customAfter removal of insoluble materials
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated to dryness
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-490f5ed6fd034cfc9f921723c0596a31
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Linked notes

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