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Bromobenzene is prepared by the action of bromine on benzene in the presence of Lewis acid catalysts such as aluminium chloride or ferric bromide. [3] Bromobenzene is used to introduce a phenyl group into other compounds. One method involves its conversion to the Grignard reagent, phenylmagnesium bromide.
Bromobenzenes may be carboxylated into carboxylic acids using carbon monoxide.The reaction takes place in a two-phase mixture of p-xylene and water as solvent, in the presence of catalytic PdCl
4-Fluorobromobenzene is synthesized via bromination of fluorobenzene in the presence of a Lewis acid catalyst such as iron(III) bromide or aluminium tribromide. [2]4-Bromofluorobenzene is regarded by the Toxic Substances Control Act as a high production volume chemical, that is, a chemical that 1 million pounds (about 500 tonnes) per year is either produced in or imported to the United States.
Benzyl bromide is used in organic synthesis for the introduction of the benzyl groups when the less expensive benzyl chloride is insufficiently reactive. [6] [7] Benzylations are often achieved in the presence of catalytic amounts of sodium iodide, which generates the more reactive benzyl iodide in situ. [3]
Bromobenzene can be converted to benzoic acid by "carboxylation" of the intermediate phenylmagnesium bromide. [15] This synthesis offers a convenient exercise for students to carry out a Grignard reaction , an important class of carbon–carbon bond forming reaction in organic chemistry.
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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.
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