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

HRID 929379ノート

反応式

HRID 929379 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a55630c50e2e445baf781239712b64d1
出典データセット
uspto-grants-2016_03
特許番号
US09295729B2

反応ノート

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