4-Fluoroaniline → N-(4-fluorophenyl)pyrrole

HRID 1748490Notes

Reaction equation

HRID 1748490 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>[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

4

Reactant 2

HCID 97314-FluoroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 727844N-(4-fluorophenyl)pyrroleYield 72.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Fluoroaniline (117 g) and 2,5-dimethoxytetrahydrofuran (139 g) were added to acetic acid (120 ml), stirred at reflux temperature for an hour and then the reaction solution was poured into ice water (1 l). The precipitated solid was filtered, dissolved in methanol and water was added therein. The precipitated solid was collected again by filtration to give 1-(4-fluorophenyl)pyrrole (122.7 g).

Workup

  1. temperatureat reflux temperature for an hour
  2. filtrationThe precipitated solid was filtered
  3. dissolutiondissolved in methanol
  4. additionwater was added
  5. filtrationThe precipitated solid was collected again by filtration

Sources & evidence

ORD record
ord-6d7bf4ea9a374c089dc66531a5ed5886
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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