Aniline → 3,4-Dibromo-1-phenyl-1H-pyrrole-2,5-dione

HRID 929379Notes

Reaction equation

HRID 929379 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:8][C:9]1=[C:10]([Br:16])[C:11]([O:13][C:14]1=O)=[O:12]>CC(O)=O>[C:2]1([N:1]2[C:14](=[O:13])[C:9]([Br:8])=[C:10]([Br:16])[C:11]2=[O:12])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 707272,5-Furandione, 3,4-dibromo-

Product 1

HCID 130592683,4-Dibromo-1-phenyl-1H-pyrrole-2,5-dioneYield 63.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

Aniline (72 μL, 0.788 mmol) was added to a solution of dibromomaleic anhydride (200 mg, 0.788 mmol) in AcOH (10 mL). The mixture was stirred for 3 h at RT and at 130° C. for 90 mins. After cooling, the mixture was concentrated to dryness and traces of AcOH removed by azeotrope with toluene. The tan residue was purified using silica flash chromatography (5% EtOAc/95% petroleum ether) to yield the desired compound as a pale yellow solid (166 mg, 60%). δH (600 MHz, CDCl3) 7.48 (m, 2H, ArH), 7.41 (tt, 1H, J=7.4 and 1.1 Hz, ArH), 7.33 (m, 2H, ArH); δC (150 MHz, CDCl3) 163.0, 131.0, 130.0, 129.5, 128.8, 126.2.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated to dryness and traces of AcOH
  3. customremoved by azeotrope with toluene
  4. customThe tan residue was purified

Sources & evidence

ORD record
ord-a55630c50e2e445baf781239712b64d1
Source dataset
uspto-grants-2016_03
Patent number
US09295729B2

Reaction notes

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