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Radical Bromination [Ex. 3]
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The electrophile is a halonium ion, Cl+ or Br+, formed by treating Cl2 or Br2 with AlCl3 or FeCl3:
"Chemistry" 2e - Blackman, A., Bottle, S., Schmid, S., Mocerino, M., Wille, U.
Some succinimide precitipated after a bromination of a toluene derivative using NBS (N-bromosuccinimide).
N-Bromosuccinimide or NBS is a chemical reagent used in radical substitution and electrophilic addition reactions in organic chemistry. NBS can be a convenient source of Br•, the bromine radical.
Interesting things from NBS: it is well soluble in chloroform and other halogenated solvents, but when the bromine reacts and succinimide is produced, it precipates as a white solid (what is seen at the side of the flask). Another info: NBS can be recrystallized from hot water.

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Bromination using elemental bromine as a bromine source on a relative larger, 0.5 mol scale. On the third gif the product is stirred in the bromine containing reaction mixture and luckily it precipitated, so we only need to filter it.Â
Interesting fact from Bromine:  In 1825 bromine had been isolated from sea water by Justus von Liebig who mistakenly thought it was a compound of iodine and chlorine, since it had similar chemical and physical properties to these already discovered elements. Only a year later, in 1826 by the French chemist Antoine-Jérôme Balard described bromine as a new element. He obtained bromine from the manufacture of sea salt at Montpellier by passing chlorine through an aqueous solution of the residues, which contained magnesium bromide. Distillation of the material with manganese dioxide and sulfuric acid produced red vapors, which condensed to a dark liquid.
Important note:  Don’t clean Br2-contaminated glassware with acetone, use alcohol. From the reaction of bromine and acetone bromoacetone is generated what is a potent irritant/lacrymator.
Bromination using elemental bromine.Â
Did you know that bromine is transparent in the infrared region? (above 700 nm)Â
Did you know that in old days instead of preparing anhydrous catalyst and other fancy stuff, chemists just added some iron powder when they performed a bromination? The bromine reacted in-situ with the iron to form iron(III)-bromide which acted as a catalyst for most reactions.Â
Bromination with elemental bromine in acetic acid.Â
During bromination with elemental bromine, sometimes a bromine adduct, probably Br2xAcOH or HBr3 crystallizes out what looks adorable, as seen on the above photo. It redissolves/liquefies when the concentration of the acetic acid increases in the vapor (last gif), but it looks great.
Bromine is a quite corrosive, toxic fuming liquid, therefore it should be handled with care. I wrote a lot from this element in the past, check out the previous posts: http://labphoto.tumblr.com/tagged/bromine