How will you bring out the following conversion?
How will you bring out the following conversion?
This conversion can be achieved in three steps-
1. Bromination of p−nitroaniline in polar solvent
Since the nitro group will decrease the electron density in the benzene at ortho and para position with respect to −NO2 group. So, it directs the bromonium ion at meta position with respect to the nitro group.
And amine group will increase the electron density at ortho and para position to it. Since the para position is occupied, electrophile bromonium ion will add to ortho positions respective to −NH2 group to it.
2. Diazotization of the product formed in Step-1:
3. Replacement of diazonium group by Bromide ion-
The intermediate diazonium compound is treated with Cu2Br2/HCl to obtain the desired product.
This conversion can be achieved in three steps-
1. Bromination of p−nitroaniline in polar solvent
Since the nitro group will decrease the electron density in the benzene at ortho and para position with respect to −NO2 group. So, it directs the bromonium ion at meta position with respect to the nitro group.
And amine group will increase the electron density at ortho and para position to it. Since the para position is occupied, electrophile bromonium ion will add to ortho positions respective to −NH2 group to it.
2. Diazotization of the product formed in Step-1:
3. Replacement of diazonium group by Bromide ion-
The intermediate diazonium compound is treated with Cu2Br2/HCl to obtain the desired product.
