p-Toluenesulfonic acid → 1-(3-bromophenyl)-2,5-dimethyl-1H-pyrrole

HRID 1994117ノート

反応式

HRID 1994117 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C[C:10]1[CH:11]=[CH:12][C:13](S(O)(=O)=O)=[CH:14][CH:15]=1>C(CC(=O)C)C(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[C:14]([CH3:13])=[CH:15][CH:10]=[C:11]2[CH3:12])[CH:6]=[CH:7][CH:8]=1

参加物

5

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 115623-Bromoaniline

生成物 1

HCID 47636541-(3-bromophenyl)-2,5-dimethyl-1H-pyrrole収率 96%

試薬・触媒・溶媒 2

HCID 80352,5-Hexanedione溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 3-bromoaniline (2.50 mL, 23.0 mmol) in acetonylacetone (3.00 mL, 25.6, mmol) containing a small amount of p-TSA was heated at reflux in a round bottom flask fitted with a Dean Stark trap and a reflux condenser for 5 h. The reaction mixture was allowed to cool to rt and diluted with EtOAc. The solution was washed with 1N HCl and sat. NaHCO3 solution. The organic solutions were dried over Na2SO4, filtered, and concentrated to give the desired product as a light brown solid (5.5 g, 96%) which was used without further purification.

後処理

  1. temperaturewas heated
  2. temperatureat reflux in a round bottom flask
  3. customfitted with a Dean Stark trap and a reflux condenser for 5 h
  4. washThe solution was washed with 1N HCl and sat. NaHCO3 solution
  5. dry with materialThe organic solutions were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-85da1545317a4534bbc5d18252565280
出典データセット
uspto-grants-2010_01
特許番号
US07652041B2

反応ノート

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