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

Temperature

90 °C

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).

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

ORD record

ord-484319ec540c46ffa49627196a932ac3

Source dataset

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05210092