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

HRID 1597493Notes

Reaction equation

HRID 1597493 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-7613062c459b4b3cb9923789a1ca4951
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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