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Brominating aniline with elemental bromine gives 2,4,6-tribromoaniline. This is then diazotized, then reacted with ethanol to replace the diazonium group with hydrogen, forming 1,3,5-tribromobenzene. [3] It has also been prepared by these methods: [3] replacement of the amino group of 3,5-dibromoaniline with bromine
In numerous variants that have been developed, other transition metal salts, including copper(II), iron(III) and cobalt(III) have also been employed. [7] Due to its wide synthetic applicability, the Sandmeyer reaction, along with other transformations of diazonium compounds, is complementary to electrophilic aromatic substitution.
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 .
The benzyl cation or phenylcarbenium ion is the carbocation with formula C 6 H 5 CH + 2; the benzyl anion or phenylmethanide ion is the carbanion with the formula C 6 H 5 CH − 2. None of these species can be formed in significant amounts in the solution phase under normal conditions, but they are useful referents for discussion of reaction ...
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.
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 .
In the Gattermann reaction (there are other "Gattermann reactions"), benzenediazonium chloride is warmed with copper powder and HCl or HBr to produce chlorobenzene and bromobenzene respectively. [18] 2 Cu + 2 [C 6 H 5 N 2] + → 2 Cu + + (C 6 H 5) 2 + 2 N 2 (initiation) [C 6 H 5 N 2] + + HX → C 6 H 5 X + N 2 + H + (Cu + catalysis)
This reaction differs from a common S N 2 reaction, because it happens at a trigonal carbon atom (sp 2 hybridization). The mechanism of S N 2 reaction does not occur due to steric hindrance of the benzene ring. In order to attack the C atom, the nucleophile must approach in line with the C-LG (leaving group) bond from the back, where the ...