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

HRID 1994117노트

반응식

HRID 1994117 반응식
[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

참가 물질

5

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 115623-Bromoaniline

생성물 1

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

시약·촉매·용매 2

HCID 80352,5-Hexanedione용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-85da1545317a4534bbc5d18252565280
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652041B2

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