p-Toluenesulfonic acid → 1-(4-Bromophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole

HRID 396751ノート

反応式

HRID 396751 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][CH2:13][C:14](=O)[CH3:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Br:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:18][C:19]1[CH:25]=[CH:24][C:22]([N:23]2[C:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)=[CH:12][CH:13]=[C:14]2[CH3:15])=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 78074-BromoanilineHCID 105388711-[4-(Methylsulfonyl)phenyl]-1,4-pentanedione

生成物 1

HCID 223168431-(4-Bromophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole収率 54.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 1-[4-(methylsulfonyl)phenyl]pentane-1,4-dione (3 g, 11.8 mmol), 4-bromoaniline (2.03 g, 11.8 mmol), and p-toluenesulfonic acid (150 mg) in toluene (250 mL) was heated at reflux temperature using Dean-Stark apparatus. After cooling down, volatiles were removed by evaporation. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/3) to give the subtitle compound (2.5 g, 54% yield).

後処理

  1. temperaturewas heated
  2. temperatureat reflux temperature
  3. temperatureAfter cooling down
  4. customvolatiles were removed by evaporation
  5. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/3)

出典と根拠

ORDレコード
ord-e06da88d6d144d0eac5fe404c85767ed
出典データセット
uspto-grants-2003_08
特許番号
US06608095B2

反応ノート

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