No.143
Highly Effective Brominating Reagent
| D3753 | Dibromoisocyanuric Acid (1) |
5g 25g |
Dibromoisocyanuric Acid (DBI, 1), which was first reported by Gottardi,1a) is a mild and highly effective brominating reagent.1b,2) Nitrobenzene was converted to the 3-bromo derivative in 88% yield with DBI in conc. sulfuric acid in 5 min at 20 °C, but in only 50% yield with NBS in 50% sulfuric acid in 3 h at 85 °C.1a) DBI has been widely used as an effective brominating reagent.3)
References
11) Bromination of aromatic compounds
a) W. Gottardi, Monatsh. Chem. 1968, 99, 815.[DOI] b) W. D. Brown, A. H. Gouliaev, Synthesis 2002, 83.[DOI]
2) A review of dibromoisocyanuric acid (DBI)
S. C. Virgil, Encyclopedia of Reagents for Organic Synthesis, ed. by L. A. Paquette, John, Wiley & Sons, Chichester, 2001[DOI]; 1995, pp. 1560-1561.
3) Bromination of other compounds
a) Z. P. Demko, M. Bartsch, K. B. Sharpless, Org. Lett. 2000, 2, 2221.[DOI] b) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316.[DOI]
a) W. Gottardi, Monatsh. Chem. 1968, 99, 815.[DOI] b) W. D. Brown, A. H. Gouliaev, Synthesis 2002, 83.[DOI]
2) A review of dibromoisocyanuric acid (DBI)
S. C. Virgil, Encyclopedia of Reagents for Organic Synthesis, ed. by L. A. Paquette, John, Wiley & Sons, Chichester, 2001[DOI]; 1995, pp. 1560-1561.
3) Bromination of other compounds
a) Z. P. Demko, M. Bartsch, K. B. Sharpless, Org. Lett. 2000, 2, 2221.[DOI] b) T. R. Walters, W. W. Zajac Jr., J. M. Woods, J. Org. Chem. 1991, 56, 316.[DOI]
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