Methyl 4-iodobenzoate, or methyl ''p''-iodobenzoate, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula IC₆H₄COOCH₃. It is the

methyl ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distinct ...

4-iodobenzoic acid 4-Iodobenzoic acid, or ''p''-iodobenzoic acid, is an isomer of iodobenzoic acid. Structure X-ray crystallography of 4-iodobenzoic acid has shown that it crystallizes in the solid state as hydrogen-bonded dimers which stack perpendicular to th ...

, or may also be viewed as an iodinated derivative of

methyl benzoate Methyl benzoate is an organic compound. It is an ester with the chemical formula , sometimes abbreviated as , where Ph and Me are phenyl and methyl, respectively. Its structure is . It is a colorless liquid that is poorly soluble in water, but m ...

Preparation

Methyl 4-iodobenzoate may be prepared by the

Fischer esterification Fischer is a German occupational surname, meaning fisherman. The name Fischer is the fourth most common German surname. The English version is Fisher. People with the surname A * Abraham Fischer (1850–1913) South African public official * ...

of 4-iodobenzoic acid with

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

Reactions

The aryl-iodide functionality of methyl 4-iodobenzoate may undergo

coupling reaction In organic chemistry, a coupling reaction is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid of a metal catalyst. In one important reaction type, a main group organometallic compound o ...

s, such as a symmetrical

Sonogashira coupling The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vi ...

with

trimethylsilylacetylene Trimethylsilylacetylene is the organosilicon compound with the formula . A colorless liquid, "tms acetylene", as it is also called, is used as a source of anion in organic synthesis. Use Trimethylsilylacetylene is used in Sonogashira couplin ...

(with the TMSA deprotected to

acetylene Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...

in situ) to form dimethyl 4,4'-(ethyne-1,2-diyl)dibenzoate.

References

{{reflist Benzoate esters Methyl esters 4-Iodophenyl compounds