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Fluorobenzene is an aryl fluoride and the simplest of the fluorobenzenes, with the formula C 6 H 5 F, often abbreviated PhF. A colorless liquid, it is a precursor to many fluorophenyl compounds. A colorless liquid, it is a precursor to many fluorophenyl compounds.
The Balz–Schiemann reaction (also called the Schiemann reaction) is a chemical reaction in which a primary aromatic amine is transformed to an aryl fluoride via a diazonium tetrafluoroborate intermediate. [1] [2] [3] This reaction is a traditional route to fluorobenzene and some related derivatives, [4] including 4-fluorobenzoic acid. [5]
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.
The mechanism of electrophilic fluorination remains controversial. At issue is whether the reaction proceeds via an S N 2 or single-electron transfer (SET) process. In support of the S N 2 mechanism, aryl Grignard reagents and aryllithiums give similar yields of fluorobenzene in combination with N-fluoro-o-benzenedisulfonimide (NFOBS), even though the tendencies of these reagents to ...
The diazo group (N 2) can be replaced by many other groups, usually anions, giving a variety of substituted phenyl derivatives: . C 6 H 5 N 2 + + Nu − → C 6 H 5 Nu + N 2. These transformations are associated with many named reactions including the Schiemann reaction, Sandmeyer reaction, and Gomberg-Bachmann reaction.
A classic example is the reaction of salicylic acid with a mixture of nitric and sulfuric acid to form picric acid. The nitration of the 2 position involves the loss of CO 2 as the leaving group. Desulfonation in which a sulfonyl group is substituted by a proton is a common example. See also Hayashi rearrangement.
Fluorobenzene derivatives (2 C, 37 P) Fluorobenzenes (7 P) This page was last edited on 1 November 2024, at 15:58 (UTC). Text is available under the Creative Commons ...
4,4’-Difluorobenzophenone is prepared by the acylation of fluorobenzene with p-fluorobenzoyl chloride. The conversion is typically conducted in the presence of an aluminium chloride catalyst in a petroleum ether solvent. [1] FC 6 H 4 C(O)Cl + C 6 H 5 F → (FC 6 H 4) 2 CO + HCl