Bromochlorobenzenes are mixed
aryl halide
In organic chemistry, an aryl halide (also known as a haloarene) is an aromatic compound in which one or more hydrogen atoms directly bonded to an aromatic ring are replaced by a halide ion (such as fluorine F''−'', chlorine Cl−1,−3,−5, br ...
s (
aryl chloride
In organic chemistry, an aryl halide (also known as a haloarene) is an aromatic compound in which one or more hydrogen atoms directly bonded to an aromatic ring are replaced by a halide ion (such as fluorine F''−'', chlorine Cl−1,−3,−5, bro ...
and
aryl bromide
In organic chemistry, an aryl halide (also known as a haloarene) is an aromatic compound in which one or more hydrogen atoms directly bonded to an aromatic ring are replaced by a halide ion (such as fluorine F''−'', chlorine Cl−1,−3,−5, bro ...
) consisting
bromine
Bromine is a chemical element; it has chemical symbol, symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between th ...
and
chlorine
Chlorine is a chemical element; it has Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between ...
as
substituent
In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule.
The suffix ''-yl'' is used when naming organic compounds that contain a single bond r ...
s on a
benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
ring.
All three have been synthesized by various routes:
*
1-Bromo-2-chlorobenzene: from 2-
chloroaniline Chloroaniline may refer to any of three isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of a ...
, via
diazotization
Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent, compou ...
followed by a
Sandmeyer reaction
The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts using copper salts as reagents or catalysts.
It is an example of a radical-nucleophilic aromatic substitution. The Sandmeyer reaction provides ...
*
1-Bromo-3-chlorobenzene: by (3-chlorophenyl)trimethylgermanium by
electrophilic substitution
Electrophilic substitution reactions are chemical reactions in which an electrophile displaces a functional group in a compound, which is typically, but not always, aromatic. Aromatic substitution reactions are characteristic of aromatic compounds ...
*
1-Bromo-4-chlorobenzene:
**From a derivative of (4-bromophenyl)silane using
''N''-bromosuccinimide
**From
4-chlorophenol
4-Chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pKa is 9.41.
Preparation and rea ...
using
triphenylphosphine dibromide or
phenylphosphorus tetrachloride
See also
*
Bromoiodobenzene
1-Bromo-4-iodobenzene is a mixed aryl halide (aryl bromide and aryl iodide) with the formula BrC6H4I.
Preparation
In one laboratory route to 1-bromo-4-iodobenzene, 4-bromoaniline is treated with concentrated sulfuric acid and sodium nitrite to ...
References
{{Authority control
Chlorobenzene derivatives
Bromobenzene derivatives
Mixed halobenzenes
C