N-bromobutanimide → 1-(4-Methylphenyl)-4-bromo-2-cyanopyrrole

HRID 1586782Notes

Reaction equation

HRID 1586782 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>O1CCCC1>[Br:15][C:11]1[CH:10]=[C:9]([C:13]#[N:14])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:12]=1

Participants

4

Reactant 2

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

Product 1

HCID 189562501-(4-Methylphenyl)-4-bromo-2-cyanopyrroleYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-methylphenyl)pyrrole-2-carbonitrile (1.274 g) in tetrahydrofuran (25 ml) was added N-bromosuccinimide (1.776 g) in several portions at ambient temperature. After being stirred for 3 hours at the same temperature, the mixture was concentrated in vacuo. The residue was treated with diethyl ether. The precipitates were removed by filtration and washed with a small amounts of diethyl ether. The filtrates were concentrated in vacuo to give an oily residue, which was purified by silica gel column chromatography (elution by 40% dichloromethane in n-hexane) to yield 4-bromo-1-(4-methylphenyl)pyrrole-2-carbonitrile (1.78 g) as a solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe residue was treated with diethyl ether
  3. customThe precipitates were removed by filtration
  4. washwashed with a small amounts of diethyl ether
  5. concentrationThe filtrates were concentrated in vacuo
  6. customto give an oily residue, which
  7. customwas purified by silica gel column chromatography (elution by 40% dichloromethane in n-hexane)

Sources & evidence

ORD record
ord-cffdb142855e4730967cac0465f9bc82
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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