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

HRID 1975061Notes

Reaction equation

HRID 1975061 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>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([Br:15])[CH:10]=[C:9]2[C:13]#[N:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

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

Product 1

HCID 189562501-(4-Methylphenyl)-4-bromo-2-cyanopyrrole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-methylphenyl)-2-cyanopyrrole (1.274 g) in tetrahydrofuran (25 ml) is added N-bromosuccinimide (1.776 g) in several portions at room temperature. After being stirred for 3 hours at ambient temperature, the mixture is concentrated in vacuo. The residue is treated with diethyl ether. The precipitates are removed by filtration and washed with a small amount of diethyl ether. The filtrates are concentrated in vacuo to give an oily residue, which is purified by silicagel column chromatography (elution by 40% methylene chloride in n-hexane) to yield 1-(4-methylphenyl)-4-bromo-2-cyanopyrrole as a solid.

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. additionThe residue is treated with diethyl ether
  3. customThe precipitates are removed by filtration
  4. washwashed with a small amount of diethyl ether
  5. concentrationThe filtrates are concentrated in vacuo
  6. customto give an oily residue, which
  7. customis purified by silicagel column chromatography (elution by 40% methylene chloride in n-hexane)

Sources & evidence

ORD record
ord-38b6c2f917fe4be0bf1aef398b654f2b
Source dataset
uspto-grants-1994_02
Patent number
US05284841

Reaction notes

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