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

HRID 1640161Notes

Reaction equation

HRID 1640161 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]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=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 2

HCID 80352,5-HexanedioneHCID 27358803-Bromo-5-(trifluoromethyl)aniline

Product 1

HCID 589023221-[3-bromo-5-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrroleYield 98.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A solution of 3-bromo-5-(trifluoromethyl)aniline (14.00 g, 58 mmol), hexane-2,5-dione (7.05 mL, 60 mmol) and p-toluenesulfonic acid monohydrate (220 mg, 1.2 mmol) in toluene (250 mL) was heated under Dean-Stark conditions. After 1 h, the reaction mixture was concentrated. The residue was purified by column chromatography to give 1-[3-bromo-5-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrrole (18.15 g, 98%) as orange oil. LCMS: (FA) ES+ 318.1.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9bf952b546d147a88bf2d27034ebebc9
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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