p-Toluenesulfonic acid → 1-[3-bromo-5-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrrole

HRID 1640134Notes

Reaction equation

HRID 1640134 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[CH3:13][C:14](=O)[CH2:15][CH2:16][C:17](=O)[CH3:18].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]2[CH3:13])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80352,5-HexanedioneHCID 27358803-Bromo-5-(trifluoromethyl)aniline

Product 1

HCID 589023221-[3-bromo-5-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-bromo-5-(trifluoromethyl)aniline (14.0 g, 58.3 mmol) in toluene (250 mL), was added hexane-2,5-dione (7.05 mL, 60.1 mmol) and pTSA (0.22 g, 1.20 mmol). The flask was fitted with a Dean Stark trap and reaction mixture was heated at reflux for 1 h. The mixture was allowed to cool to rt and concentrated. The residue was purified by filtration through a pad of silica to give 1-[3-bromo-5-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrrole as an orange solid (18.g g, 97.8%). 1H NMR (400 MHz, CDCl3) δ: 7.81 (s, 1H), 7.58 (s, 1H), 7.44 (s, 1H), 5.92 (s, 2H), and 2.05 (s, 6H).

Workup

  1. customThe flask was fitted with a Dean Stark trap and reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 1 h
  4. concentrationconcentrated
  5. filtrationThe residue was purified by filtration through a pad of silica

Sources & evidence

ORD record
ord-23dcbbaed59d47feba7af68893eeddf5
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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