Regiospecific Incorporation of Bromine and Iodine into Phenols Using (Trimethylsilyl)phenol Derivatives

Journal of Organic Chemistry

Volumn 48, Issue 9, 1983, Pages 1542-1544

  Wilbur, D S ^a   Stone, W E ^a   Anderson, K W ^a  

^a LOS ALAMOS NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001439897     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00157a035     Document Type: Article

References (23)

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2. Graduate Research Assistant, 1980-1981.
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5. Hashimoto, T. Yakugaku Zasshi 1967, 87, 528-529; Chem. Abstr. 1967, 67, 54206y.
6. Hashimoto, T. Yakugaku Zasshi 1960, 80, 1399-1404; Chem. Abstr. 1961, 55, 5393.
7. Eaborn, C.; Webster, D.E. J. Chem. Soc. 1960, 179-183.
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10. Wilbur, D.S.; Anderson, K.W. J. Org. Chem. 1982, 47, 358-359.
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12. Hashimoto, T. Yakugaku Zasshi 1967, 87, 530-534; Chem. Abstr. 1967, 67, 54207z.
13. Room-temperature radiobrominations (Na77BrrTBHC/MeOH) and radioiodinations (Na131I/NCS/HOAc) gave radiochemical yields of 80-90% for both ortho- and poro-(trimethylsilyl)anisoles.
14. These radionuclides are of particular interest because of their gamma decay characteristics; for example, iodine-123 has a principal gamma emission (83%) of 159 keV, which is ideal for gamma cameras currently in use, and bromine-75 is a positron emitter and may have applications in positron emission tomography.
15. Wilbur, D.S.; Anderson, K.W.; Stone, W.E.; O'Brien, H.A., Jr. J. Labelled Compd. Radiopharm. 1982, 19, 1171-1188.
16. No-carrier-added terminology is used to describe radionuclide preparations that contain only one nuclide of an element, with the stable nuclide(s) present being unintentionally added through reagent contaminants, etc. In such a preparation of bromine-77, there are theoretically only-1013 atoms of bromide present to react.
17. The in vivo stability is important as free iodide can greatly increaee the radiation dosage to the thyroid.
18. Habich, D.; Effenberger, F. Synthesis 1979, 841-876.
19. Mintz, M.J.; Walling, C. “Organic Synthesis”; Wiley: New York, 1973; Collect. Vol. 5, p. 1058.
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