Acetic Acid → N-(4-fluorophenyl)pyrrole

HRID 1744482Notes

Reaction equation

HRID 1744482 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.CO[CH:11]1[CH2:15][CH2:14][CH:13](OC)O1.C(O)(=O)C>O>[F:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH:11]=[CH:15][CH:14]=[CH:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 97314-FluoroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 727844N-(4-fluorophenyl)pyrroleYield 107.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Fluoroaniline (100 g) and 2,5-dimethoxytetrahydrofuran (124.9 g) were added to acetic acid (500 ml) and the mixture was stirred at a refluxing temperature for 1 h. After cooling to room temperature, the reaction mixture was added to water (2.5 Liters) and the mixture was stirred further for 30 min. The precipitated crystals were recrystallized from a mixed solvent of methanol-acetone (ratio=2:1) to give 1-(4-fluorophenyl)pyrrole (156 g), melting point: 57–58° C.

Workup

  1. stirringthe mixture was stirred further for 30 min
  2. customThe precipitated crystals were recrystallized from a mixed solvent of methanol-acetone (ratio=2:1)

Sources & evidence

ORD record
ord-f43c907ac724418bb7d8067c5f95e2dd
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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