mnick12 - 1-5-2011 at 13:36
Hello everyone,
I recently prepared a small amount of 1-bromo-3-nitrobenzene from sulfuric acid, potassium bromate, and nitrobenzene. The reaction went just as
described in the article provided by DJF90. Anyway I know have a small amount of 1-bromo-3-nitrobenzene that I would like to reduce to 3-bromoaniline.
What would be the best way to reduce the NO2 to NH2 without affecting the Br? I know aromatic nitro's are easy to reduce, I just would like some help
determining which ways work the best. Would Zn and acetic acid work?
Thanks
AndersHoveland - 2-5-2011 at 13:51
This may be relevant:
"investigated an industrial Ni/kieselguhr catalyst with 50% Ni, also in a flow-type catalytic apparatus
at atmospheric pressure. In a catalytic tube, it was found that this catalyst reduces p-chloronitrobenzene
to p-chloroaniline under optimum conditions (150 ~ rate of passage of p-chloronitrobenzene
0.15 ml/min, rate of delivery of hydrogen 35 ml/min) to an extent pf 64%, with 0.8% splitting out of HCl.
Increasing the temperature of the experiment promoted dehalogenation, while lowering the temperature led to a decrease in the yield of
p-chloroaniline"
Catalytic reduction of chloronitrobenzene to chloroanilines.
Reduction in the presence of nickel catalysts
N. P. Sokolova, A. A. Balandin, N. P. Maksimova
However, 4-chloro nitrobenzene may be easier to reduce than the 3-bromo nitrobenzene you are asking about, since in the first instance, the amine
group which is to be formed will be electron donating to the nitro group.
[Edited on 2-5-2011 by AndersHoveland]