Preparation of ortho-bromonitrobenzene:
1. Nitration of bromobenzene
Bromobenzene reacts with a mixture of concentrated nitric acid and concentrated sulfuric acid to give a mixture of ortho- and para-nitrobromobenzenes. The ortho isomer predominates at low temperatures, while the para isomer predominates at high temperatures.
2. Bromination of nitrobenzene
Nitrobenzene reacts with bromine in the presence of iron(III) bromide as a catalyst to give a mixture of ortho- and para-bromonitrobenzenes. The ortho isomer predominates.
Preparation of meta-bromonitrobenzene:
1. Nitration of bromobenzene
Bromobenzene reacts with a mixture of concentrated nitric acid and concentrated sulfuric acid to give a mixture of ortho- and para-nitrobromobenzenes. The para isomer predominates at high temperatures. The meta isomer can be obtained by separating the ortho and para isomers by crystallization or distillation and then reducing the para isomer to aniline, which can then be brominated to give meta-bromonitrobenzene.
2. Bromination of nitrobenzene
Nitrobenzene reacts with bromine in the presence of iron(III) bromide as a catalyst to give a mixture of ortho- and para-bromonitrobenzenes. The para isomer predominates. The meta isomer can be obtained by separating the ortho and para isomers by crystallization or distillation and then reducing the para isomer to aniline, which can then be brominated to give meta-bromonitrobenzene.
Preparation of para-bromonitrobenzene:
1. Nitration of bromobenzene
Bromobenzene reacts with a mixture of concentrated nitric acid and concentrated sulfuric acid to give a mixture of ortho- and para-nitrobromobenzenes. The para isomer predominates at high temperatures.
2. Bromination of nitrobenzene
Nitrobenzene reacts with bromine in the presence of iron(III) bromide as a catalyst to give a mixture of ortho- and para-bromonitrobenzenes. The para isomer predominates.