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

HRID 1994117Notes

Reaction equation

HRID 1994117 reaction equation
[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

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 115623-Bromoaniline

Product 1

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

Reagents, catalysts & solvents 2

HCID 80352,5-HexanedioneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-85da1545317a4534bbc5d18252565280
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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