4-Fluoroaniline → 1-(4-Fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)pyrrole

HRID 1585056Notes

Reaction equation

HRID 1585056 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][CH2:13][C:14](=O)[CH3:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:18][C:19]1[CH:25]=[CH:24][C:22]([N:23]2[C:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)=[CH:12][CH:13]=[C:14]2[CH3:15])=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 97314-FluoroanilineHCID 105388711-[4-(Methylsulfonyl)phenyl]-1,4-pentanedione

Product 1

HCID 27657241-(4-Fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)pyrroleYield 79.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1-(4-methylsulfonylphenyl)-1,4-pentanedione (580 mg, 2.28 mmol) of Step 2, 4-fluoroaniline (0.24 ml, 2.5 mmol) and p-toluenesulfonic acid (30 mg) in toluene (50 ml) was heated to reflux for 20 hours. The reaction mixture was cooled, filtered and concentrated. The crude mixture (820 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3) to give 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl)-1H-pyrrole (595 mg, 79%) as a white solid: mp (DSC) 157° C. Anal Calc'd. for C18H16NSO2F: C, 65.64; H, 4.90; N, 4.25; S, 9.73. Found: C, 65.44; H, 5.05; N, 4.16; S, 9.90.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude mixture (820 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3)

Sources & evidence

ORD record
ord-f7e49e5e94fc40d2a5be01c6b594bd3b
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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