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

HRID 929379노트

반응식

HRID 929379 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a55630c50e2e445baf781239712b64d1
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09295729B2

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