N-bromobutanimide → HCID 18436881, compound

HRID 456652Notes

Reaction equation

HRID 456652 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([C:13]1[NH:14][CH:15]=[CH:16][CH:17]=1)=[O:12].C1C(=O)N([Br:25])C(=O)C1>C1COCC1>[Br:25][C:16]1[CH:17]=[C:13]([C:11]([C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[Cl:1])=[O:12])[NH:14][CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18436869HCID 18436869, compound

Product 1

HCID 18436881HCID 18436881, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2-chloro-5-nitro-phenyl)-(1H-pyrrol-2-yl)-methanone (600 mg, 2.4 mmol) (from Aldrich, Milwaukee, Wis.) and NBS (504 mg, 2.8 mmol) in THF (60 mL) was stirred at room temperature for overnight. The reaction was concentrated, diluted with ethyl acetate (100 mL), washed wit 1N NaOH, brine and concentrated. The residue was recrystallized to give 310 mg (39%) of (4-bromo-1H-pyrrol-2-yl)-(2-chloro-5-nitro-phenyl)-methanone.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with ethyl acetate (100 mL)
  3. washwashed wit 1N NaOH, brine
  4. concentrationconcentrated
  5. customThe residue was recrystallized

Sources & evidence

ORD record
ord-82e18c5cba664a1988cb654a0bf8d6fd
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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