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4-Bromoaniline is a compound where an aniline molecule is substituted with a bromine atom on the para position. Commercially available, this compound may be used as a building block, e.g. in the preparation of monobrominated biphenyl via the Gomberg-Bachmann reaction .
Bromobenzene is an aryl bromide and the simplest of the bromobenzenes, consisting of a benzene ring substituted with one bromine atom. Its chemical formula is C 6 H 5 Br . It is a colourless liquid although older samples can appear yellow.
Phenylmagnesium bromide is prepared by reaction of bromobenzene with magnesium metal. Phenylmagnesium bromide is commercially available as solutions of diethyl ether or THF. Laboratory preparation involves treating bromobenzene with magnesium metal, usually in the form of turnings.
The reaction was first used by Antoine Béchamp to reduce nitronaphthalene and nitrobenzene to naphthylamine and aniline, respectively. [3] The Béchamp reduction is broadly applicable to aromatic nitro compounds. [4] [5] Aliphatic nitro compounds are however more difficult to reduce, often remaining as the hydroxylamine. Tertiary aliphatic ...
Aniline (from Portuguese anil ' indigo shrub ', and -ine indicating a derived substance) [6] is an organic compound with the formula C 6 H 5 NH 2. Consisting of a phenyl group ( −C 6 H 5 ) attached to an amino group ( −NH 2 ), aniline is the simplest aromatic amine .
Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis. [3] It is a precursor to diphenylmethanimine via reaction with phenylmagnesium bromide followed by methanolysis.
Since the C–I bond is weaker than C–Br or C–Cl, iodobenzene is more reactive than bromobenzene or chlorobenzene. Iodobenzene reacts readily with magnesium to form the Grignard reagent, phenylmagnesium iodide. Phenylmagnesium iodide, like the bromide analog, is a synthetic equivalent for the phenyl anion synthon.
For example, aniline has resonance structures with negative charges around the ring system: The amino group can donate electron density through resonance. Attack occurs at ortho and para positions, because the (partial) formal negative charges at these positions indicate a local electron excess.