Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions
Abstract
:1. Introduction
2. Results and Discussion
2.1. Selective Synthesis of IBA and Its Analogs
2.2. IBAs Synthesis Using Ferric Effect
2.3. IBA Derivatives
3. Materials and Methods
3.1. General Information
3.2. Synthesis of IBA Analogues
3.2.1. General Procedure for the Synthesis of IBAs 2a–v and 4
3.2.2. 1-Hydroxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2a)
3.2.3. 5-Fluoro-1-hydroxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2b)
3.2.4. 5-Chloro-1-hydroxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2c)
3.2.5. 5-Bromo-1-hydroxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2d)
3.2.6. 1-Hydroxy-5-methyl-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2e)
3.2.7. 1-Hydroxy-5-methoxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2f)
3.2.8. 1-Hydroxy-3-oxo-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxol-5-yl acetate (2g)
3.2.9. 1-Hydroxy-5-(trifluoromethyl)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2h)
3.2.10. 1-Hydroxy-5-nitro-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2i)
3.2.11. 1-Hydroxy-3-oxo-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole-5-carbonitrile (2j)
3.2.12. 1,5-Dihydroxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2k)
3.2.13. 6-Fluoro-1-hydroxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2l)
3.2.14. 6-Chloro-1-hydroxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2m)
3.2.15. 6-Bromo-1-hydroxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2n)
3.2.16. 1-Hydroxy-6-(trifluoromethyl)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2o)
3.2.17. 1-Hydroxy-3-oxo-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole-6-carboxylic acid (2p)
3.2.18. 5,6-Difluoro-1-hydroxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2q)
3.2.19. 1-Hydroxy-5,6-dimethoxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2r)
3.2.20. 7-Bromo-1-hydroxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2s)
3.2.21. 1-Hydroxy-7-methyl-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2t)
3.2.22. 4-Fluoro-1-hydroxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2u)
3.2.23. 1-Hydroxy-4-methyl-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (2v)
3.2.24. 1-Hydroxy-1λ3-naphtho[2,3-d][1,2]iodaoxol-3(1H)-one (4)
3.3. Synthesis of Benziodoxole Alkoxides
3.3.1. General Procedure for the Synthesis of Benziodoxole Alkoxides (6)
3.3.2. 1-Methoxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (6a)
3.3.3. 1-Ethoxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (6b)
3.3.4. 1-(2,2,2-trifluoroethoxy)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (6c)
3.3.5. 1-Propoxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (6d)
3.3.6. 1-Isopropoxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (6e)
3.3.7. 1-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (6f)
3.3.8. 1-Butoxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (6g)
3.3.9. 1-(tert-Butoxy)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (6h)
3.4. Synthesis of Benziodoxole Acetates
3.4.1. General Procedure for the Synthesis of Benziodoxole Acetates (7)
3.4.2. 3-Oxo-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl acetate (7a)
3.4.3. 5-Fluoro-3-oxo-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl acetate (7b)
3.4.4. 5-Chloro-3-oxo-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl acetate (7c)
3.4.5. 5-Bromo-3-oxo-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl acetate (7d)
3.4.6. 5-Methyl-3-oxo-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl acetate (7e)
3.4.7. 5-Methoxy-3-oxo-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl acetate (7f)
3.4.8. 3-Oxo-1λ3-benzo[d][1,2]iodaoxole-1,5(3H)-diyl diacetate (7g)
3.4.9. 3-Oxo-5-(trifluoromethyl)-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl acetate (7h)
3.4.10. 5-Nitro-3-oxo-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl acetate (7i)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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China, H.; Kageyama, N.; Yatabe, H.; Takenaga, N.; Dohi, T. Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions. Molecules 2021, 26, 1897. https://doi.org/10.3390/molecules26071897
China H, Kageyama N, Yatabe H, Takenaga N, Dohi T. Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions. Molecules. 2021; 26(7):1897. https://doi.org/10.3390/molecules26071897
Chicago/Turabian StyleChina, Hideyasu, Nami Kageyama, Hotaka Yatabe, Naoko Takenaga, and Toshifumi Dohi. 2021. "Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions" Molecules 26, no. 7: 1897. https://doi.org/10.3390/molecules26071897