Methyl 4-iodobenzoate explained

Methyl 4-iodobenzoate, or methyl p-iodobenzoate, is an organic compound with the formula IC₆H₄COOCH₃.^[1] It is the methyl ester of 4-iodobenzoic acid, or may also be viewed as an iodinated derivative of methyl benzoate.

Preparation

Methyl 4-iodobenzoate may be prepared by the Fischer esterification of 4-iodobenzoic acid with methanol.^[2]

Reactions

The aryl-iodide functionality of methyl 4-iodobenzoate may undergo coupling reactions, such as a symmetrical Sonogashira coupling with trimethylsilylacetylene (with the TMSA deprotected to acetylene in situ) to form dimethyl 4,4'-(ethyne-1,2-diyl)dibenzoate.^{[2] [3]}

Notes and References

1. Web site: PubChem . Methyl 4-iodobenzoate . 24 October 2023 . . en.
2. Gadzikwa . Tendai . Zeng . Bi-Shun . Hupp . Joseph T. . Nguyen . SonBinh T. . 2008 . Ligand-elaboration as a strategy for engendering structural diversity in porous metal–organic framework compounds . . 31 . 3672–3674 . 10.1039/B714160B. 18665295 .
3. Mio . Matthew J. . Kopel . Lucas C. . Braun . Julia B. . Gadzikwa . Tendai L. . Hull . Kami L. . Brisbois . Ronald G. . Markworth . Christopher J. . Grieco . Paul A. . 2002 . One-Pot Synthesis of Symmetrical and Unsymmetrical Bisarylethynes by a Modification of the Sonogashira Coupling Reaction . . 4 . 19 . 3199–3202 . 10.1021/ol026266n. 12227748.