4-bromoaniline can be prepared by aniline easily. Aniline is an ortho para activator. In 4-bromoaniline bromine atom exist in para position related to the amine group.
But reaction of aniline and bromine liquid will give 2,4,6-tribromoaniline. Therefore we have to control the reaction if we need to prepare 4-bromoaniline.
Question: Derive 4-bromoaniline from benzene
Aniline is a ortho para activator. When liquid bromine (Br2(l)) is added to the aniline, it gives 2,4,6-bromoaniline.
But we need only one bromine atom to connect to the para position of aniline. Therefore we reduce the activity of aniline by the reaction of aniline and ethanoyl chloride (CH3COCl). Then we add Br2(l) to thenewly formed compound.
Aniline is a strong ortho para activator. Aniline and ethanoyl chloride react to give N-phenylethanamide which is a ortho para Moderate activator. This product is an amide compound.
-NH-CO-CH3 group results a steric impediment around that group. Therefore, substitutions to ortho places is more difficult than para places.
Two products are given. Due to steric impediment, bromine is substituted more to para position. Therefore major product is para substituted compound.
Reaction between aniline and liquid bromium will give 2,4,6-tribromoaniline. 2,4,6-tribromoaniline is a white precipitate.
We cannot prepare m-bromoaniline in one step from aniline because aniline is a ortho - para activator. In m-bromoaniline, bromine atom is attached to the meta position of aniline. We have to convert aniline to a deactivater and then attach bromine atom to the meta position.
p-bromoaniline | para-bromoaniline
There are three steps in preparation of 4-bromoaniline from aniline.
Phenyl amine is aniline. The conversion of aniline to 4-bromoaniline is explained above.