Elsevier

Chinese Chemical Letters

Volume 21, Issue 8, August 2010, Pages 914-918
Chinese Chemical Letters

A simple and efficient method for solvent-free iodination of hydroxylated aromatic aldehydes and ketones using iodine and iodic acid by grinding method

https://doi.org/10.1016/j.cclet.2010.04.008Get rights and content

Abstract

Green, mild and efficient iodination of hydroxylated aromatic aldehydes and ketones using iodine and iodic acid in the solid-state by grinding under solvent-free conditions at room temperature. This method provides several advantages such as environmentally friendly, short reaction times, high yields, non-hazardous and simple work-up procedure.

Section snippets

Experimental

Melting points were determined in an open capillary tube and are uncorrected. IR spectra were recorded in KBr on a PerkinElmer spectrometer. 1H NMR spectra were recorded on a Gemini 300-MHz instrument in CDCl3 as solvent and TMS as an internal standard. Elemental analysis was carried out on a Carlo Erba 1108 analyzer. All the products were identified by comparison of their spectral and physical data with those of the known sample. The purity of products was checked by thin-layer chromatography

Result and discussion

In continuation of our earlier research works on iodination of some aromatics [23], [24], [25], [26], [27], [28], [29], herein, first time we would like to report a simple, efficient and solvent-free iodination of hydroxylated aromatic aldehydes and ketones using iodine and iodic acid by grinding method (Scheme 1).

A combination of iodine and iodic acid has been found to be an excellent reagent for the efficient iodination of hydroxylated aromatic aldehydes and ketones. These reactions are

Conclusion

In conclusion, we have reported a simple and efficient method for solvent-free iodination of hydroxylated aromatic aldehydes and ketones using iodine and iodic acid by grinding method. The notable merits of the present method are shorter reaction times (20–30 min), simple work-up procedure; high yield (82–94%), environmentally friendly as it does not use any auxiliary or organic solvent. To the best of our knowledge this is first repot on iodination of hydroxylated aromatic aldehydes and ketones

Acknowledgments

Authors are also grateful to UGC New Delhi for sanctioning Major Research Grant and the Director, IICT, Hyderabad for providing spectral analysis. The authors are thankful to Principal, Yeshwant Mahavidyalaya, Nanded for providing laboratory facilities.

References (30)

  • R.H. Seevers et al.

    Chem. Rev.

    (1982)
  • S.M. Hubig et al.

    J. Org. Chem.

    (1994)
  • K. Elbs et al.

    J. Proki. Chem.

    (1913)
  • D.M. Marko et al.

    Khim. Referat. Zhur.

    (1941)
  • Y.B. Vibhute et al.

    J. Indian Chem. Soc.

    (1981)
  • W. Tong et al.

    J. Biol. Chem.

    (1954)
  • G.W. Wang et al.

    Org. Lett.

    (2009)
    G.W. Wang et al.

    J. Org. Chem.

    (2008)
    X.L. Wu et al.

    Org. Biomol. Chem.

    (2008)
    Y.W. Dong et al.

    Tetrahedron

    (2008)
    G.W. Wang et al.

    Adv. Synth. Catal.

    (2007)
  • K. Tanaka et al.

    Chem. Rev.

    (2000)
  • M. Veit et al.

    Chem. Ing. Tech.

    (1996)
    K. Tanaka et al.

    J. Org. Chem.

    (1991)
    F. Toda et al.

    J. Chem. Soc. Perkin Trans.

    (1990)
    F. Toda et al.

    J. Chem. Soc. Perkin Trans.

    (1998)
  • F. Diederich et al.

    Metal Catalysed Cross Coupling Reactions

    (1988)
  • R.C. Larock et al.

    J. Org. Chem.

    (1991)
    R.C. Larock et al.

    J. Am. Chem. Soc.

    (1991)
    C.A. Busacca et al.

    Tetrahedron Lett.

    (1992)
    J.S. Swenton et al.

    J. Org. Chem.

    (1992)
  • R.H. Seevers et al.

    Chem. Rev.

    (1982)
    K.C. Nicolaou

    Angew. Chem. Int. Ed. Engl.

    (1993)
  • M. Sovak

    Radiocontrast Agents: Handbook of Experimental Pharmacology

    (1993)
  • Y. Noda et al.

    Tetrahedron Lett.

    (1997)
  • Cited by (20)

    • Iodine(iii) reagents for oxidative aromatic halogenation

      2022, Organic and Biomolecular Chemistry
    • Grindstone chemistry: A “green” approach for the synthesis and derivatization of heterocycles

      2022, Tetrahedron
      Citation Excerpt :

      The nanocatalyst was prepared by the group and its reusability study showed that it could be used up to 5 cycles without much decrease in its catalytic activity (83% effective). In another study, Vibhute and coworkers developed a hand-grinding protocol for the iodination of phenols with aldehyde and ketone functionalities by a combination of iodine and iodic acid [123]. The mechanochemical Vilsmeier-Haack reaction was reported by Mohammed et al. for formylation and acylation of various anisoles (57) and pyridines (58) by grinding them vigorously with Vilsmeier-Haack reagent, 59 to give the desired products (60 and 61) using a mortar and pestle (Fig. 5d) [124].

    • Fluorescence analysis of iodinated acetophenone derivatives

      2015, Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
      Citation Excerpt :

      Additionally, iodinated aromatic compounds are also important building blocks used in the synthesis of biologically active products [5], for instance, being usually related to the production of new hormone derivatives in the thyroid gland [6]. In fact, they are widely applied as drugs and diagnostic agents in medicine [7,8]. As recently reported by Gallo et al. [9], it is possible to obtain significant yields of iodinated aromatic compounds derived from 4-hydroxyacetophenone under mild reaction conditions.

    View all citing articles on Scopus
    View full text