2-Bromo-4-methylaniline → 1-(2-bromo-4-methylphenyl)-1H-pyrrole

HRID 1586791Notes

Reaction equation

HRID 1586791 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].CO[CH:12]1[CH2:16][CH2:15][CH:14](OC)O1>C(O)(=O)C>[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[N:4]1[CH:12]=[CH:16][CH:15]=[CH:14]1

Participants

4

Reactant 2

HCID 114222-Bromo-4-methylanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 47151991-(2-bromo-4-methylphenyl)-1H-pyrroleYield 84.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

2-Bromo-4-methylaniline (15.0 g), 2,5-dimethoxytetrahydrofuran (10.7 g) and acetic acid (81 ml) were combined under nitrogen atmosphere. The reaction mixture was stirred at 90° C. for 1.5 hours. After being cooled to room temperature, the reaction mixture was concentrated in vacuo with toluene. n-Hexane (300 ml) was added to the residue, and the suspension was filtered through Celite. Then silica gel was added to the filtrate with stirring until the colour of the solution disappeared. The suspension was filtered and the filtrate was concentrated in vacuo to give 1-(2-bromo-4-methylphenyl)pyrrole (16.1 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. concentrationthe reaction mixture was concentrated in vacuo with toluene
  3. additionn-Hexane (300 ml) was added to the residue
  4. filtrationthe suspension was filtered through Celite
  5. additionThen silica gel was added to the filtrate
  6. stirringwith stirring until the colour of the solution
  7. filtrationThe suspension was filtered
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-203146b8aae74d2ca2a57d3cf684eee6
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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