4-Bromoaniline → 1-(4-Bromophenyl)-2-(3-fluoro-4-(methylsulfonyl)phenyl]-5-methyl-1H-pyrrole

HRID 2086634Notes

Reaction equation

HRID 2086634 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12](=O)[CH2:13][CH2:14][C:15](=O)[CH3:16])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:19][C:20]1[CH:26]=[CH:25][C:23]([N:24]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[C:4]2[CH:5]=[CH:6][C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:2]([F:1])[CH:3]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 78074-BromoanilineHCID 223169711-[3-Fluoro-4-(methylsulfonyl)phenyl]pentane-1,4-dione

Product 1

HCID 223168021-(4-Bromophenyl)-2-(3-fluoro-4-(methylsulfonyl)phenyl]-5-methyl-1H-pyrroleYield 95.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1-[3-fluoro-4-(methylsulfonyl)phenyl]pentane-1,4-dione (2.8 g, 10.3 mmol), 4-bromoaniline (2.12 g, 12.3 mmol), and p-toluenesulfonic acid (150 mg) in toluene (250 mL) was heated at reflux temperature using Dean-Stark apparatus. After cooling down, volatiles were removed by evaporation. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/5) to give the subtitle compound (4 g, 95% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature
  3. temperatureAfter cooling down
  4. customvolatiles were removed by evaporation
  5. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/5)

Sources & evidence

ORD record
ord-6d6577c1a2044ad9aa1aad4936ec75e4
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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