Hydrogen Bromide†
Gary W. Breton,
Paul J. Kropp,
Gary W. Breton
University of North Carolina, Chapel Hill, NC, USA
Search for more papers by this authorPaul J. Kropp
University of North Carolina, Chapel Hill, NC, USA
Search for more papers by this authorGary W. Breton,
Paul J. Kropp,
Gary W. Breton
University of North Carolina, Chapel Hill, NC, USA
Search for more papers by this authorPaul J. Kropp
University of North Carolina, Chapel Hill, NC, USA
Search for more papers by this authorFirst published: 15 April 2001
Abstract
[10035-10-6] BrH (MW 80.91)
InChI = 1S/BrH/h1H
InChIKey = CPELXLSAUQHCOX-UHFFFAOYSA-N
(reagent for electrophilic5 and radical-mediated1b hydrobromination of alkenes and alkynes; cleaves epoxides1c and ethers;20 converts alcohols13 and chlorides32 to bromides; converts α-diazo ketones to α-bromomethyl ketones,28a and 1,4-cyclohexanediones to phenols29)
Alternate Name: Hydrobromic Acid
Solubility: sol most organic solvents.2
Form Supplied in: widely available as compressed gas; 30% solution in AcOH or EtCO2H; 48% aqueous solution.
Preparative Method: can be generated in situ by treatment of refluxing tetrahydronaphthalene with Br2;3 treatment of Ph3PHBr with refluxing xylene.4
Handling, Storage, and Precautions: highly toxic and corrosive. This reagent should be handled in a fume hood.
Bibliography
- 1(a)
Larock, R. C.;
Leong, W. W.
Comprehensive Organic Synthesis
1991,
4,
269.
10.1016/B978-0-08-052349-1.00096-2 Google Scholar(b) Stacey, F. W.; Harris, Jr., J. F. Org. React. 1963, 13, 150. (c) Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737.
- 2 Fogg, P. G. T.; Gerrard, W.; Clever, H. L. In Solubility Data Series; J. W. Lorimer, Ed.; Pergamon: Oxford, 1990; Vol. 42.
- 3
Maxson, R. N.
Inorg. Synth.
1939,
1,
149.
10.1002/9780470132326.ch53 Google Scholar
- 4 Hercouet, A.; Le Corre, M. Synthesis 1988, 157.
- 5(a) Kropp, P. J.; Daus, K. A.; Crawford, S. D.; Tubergen, M. W.; Kepler, K. D.; Craig, S. L.; Wilson, V. P. J. Am. Chem. Soc. 1990, 112, 7433. (b) Kropp, P. J.; Daus, K. A.; Tubergen, M. W.; Kepler, K. D.; Wilson, V. P.; Craig, S. L.; Baillargeon, M. M.; Breton, G. W. J. Am. Chem. Soc. 1993, 115, 3071. (c) Kropp, P. J.; Crawford, S. D. J. Org. Chem. 1994, 59, 3102.
- 6 Walling, C. Free Radicals in Solution; Wiley: New York, 1957; pp 291–296.
- 7 Landini, D.; Rolla, F. J. Org. Chem. 1980, 45, 3527.
- 8 Walborsky, H. M.; Topolski, M. J. Am. Chem. Soc. 1992, 114, 3455.
- 9(a) Boeckman, Jr., R. K.; Blum, D. M. J. Org. Chem. 1974, 39, 3307. (b) Cousseau, J. S. 1980, 805. (c) Hara, S.; Dojo, H.; Takinami, S.; Suzuki, A. Tetrahedron Lett. 1983, 24, 731.
- 10(a) Buchanan, J. G.; Sable, H. Z. In Selective Organic Transformations; B. S. Thyagarajan, Ed.; Wiley: New York, 1972; Vol. 2, pp 1–92. (b) Armarego, W. L. F. In Stereochemistry of Heterocyclic Compounds; E. C. Taylor; A. Weissberger, Eds.; Wiley: New York, 1977; pp 23–25. (c) Bartok, M.; Lang, K. L. In The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulfur Analogues; S. Patai, Ed.; Wiley: New York, 1980; Part 2, pp 655–659.
- 11 Stewart, C. A.; VanderWerf, C. A. J. Am. Chem. Soc. 1954, 76, 1259.
- 12(a) Reid, E. E.; Ruhoff, J. R.; Burnett, R. E. Org. Synth., Coll. Vol. 1943, 2, 246. (b) McEwen, W. L. Org. Synth., Coll. Vol. 1955, 3, 227.
- 13 Doxsee, K. M.; Feigel, M.; Stewart, K. D.; Canary, J. W.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1987, 109, 3098.
- 14 Vogel, A. I. J. Chem. Soc 1943, 636.
- 15 Kamm, O.; Marvel, C. S. Org. Synth., Coll. Vol. 1941, 1, 25.
- 16 Dakka, G.; Sasson, Y. Tetrahedron Lett. 1987, 28, 1223.
- 17 Masada, H.; Murotani, Y. Bull. Chem. Soc. Jpn. 1980, 53, 1181.
- 18(a) Golding, B. T.; Hall, D. R.; Sakrikar, S. J. Chem. Soc., Perkin Trans. 1 1973, 1214. (b) Ellis, M. K.; Golding, B. T. Org. Synth., Coll. Vol. 1990, 7, 356.
- 19 Allen, C. F. H.; Bell, A. Org. Synth., Coll. Vol. 1955, 3, 312.
- 20 Parham, W. E.; Sayed, Y. A. Synthesis 1976, 116.
- 21 Bhatt, M. V.; Kulkarni, S. U. Synthesis 1983, 249.
- 22(a) Andrus, D. W. Org. Synth., Coll. Vol. 1941, 3, 692. (b) Newkome, G. R.; Gupta, V. K.; Griffin, R. W.; Arai, S. J. Org. Chem. 1987, 52, 5480.
- 23 Landini, D.; Montanari, F.; Rolla, F. Synthesis 1978, 771.
- 24(a) Clarke, H. T.; Taylor, E. R. Org. Synth., Coll. Vol. 1941, 1, 150. (b) Surrey, A. R. Org. Synth., Coll. Vol. 1955, 3, 753.
- 25(a) Lavety, J.; Proctor, G. R. Org. Synth., Coll. Vol. 1973, 5, 545. (b) ApSimon, J.; Seguin, R. Synth. Commun. 1980, 10, 897.
- 26 Bestmann, H. J.; Mott, L.; Lienert, J. Justus Liebigs Ann. Chem./Liebigs Ann. Chem. 1967, 709, 105.
- 27
Bodansky, M.;
Bodansky, A. In
The Practice of Peptide Synthesis;
Springer:
New York,
1984;
pp 165–168.
10.1007/978-3-642-96835-8 Google Scholar
- 28 Chambers, R. A.; Pearson, D. E. J. Org. Chem. 1963, 28, 3144.
- 29(a) Catch, J. R.; Elliott, D. F.; Hey, D. H.; Jones, E. R. H. J. Chem. Soc 1948, 278. (b) Balenovic, K.; Cerar, D.; Filipovic, L. J. Org. Chem. 1953, 18, 868.
- 30 Rao, C. G.; Rengaraju, S.; Bhatt, M. V. Chem. Commun./J. Chem. Soc., Chem. Commun. 1974, 584.
- 31(a) Bradsher, C. K.; Winston, Jr., J. J. J. Am. Chem. Soc. 1954, 76, 734. (b) Canonne, P.; Holm, P.; Leitch, L. C. Can. J. Chem. 1967, 45, 2151.
- 32 Madesclaire, M. Tetrahedron 1988, 44, 6537.
- 33 Yoon, K. B.; Kochi, J. K. J. Org. Chem. 1989, 3028.
- 34 Svetlakov, N. V.; Moisak, I. E.; Averko-Antonovich, I. G. J. Org. Chem. USSR (Engl. Transl.) 1969, 5, 971.
- 35(a)
Pan, H.-L.;
Fletcher, T. L.
Synthesis
1973,
610.
10.1055/s-1973-22267 Google Scholar(b) Fletcher, T. L.; Pan, H.-L.; J. Chem. Soc 1965, 4588.
- 36 Olah, G. A.; Tolgyesi, W. S. In Friedel-Crafts and Related Reactions; G. A. Olah, Ed.; Interscience: New York, 1964; Vol. 2, Part 2, pp 1–92.
- 37 Connor, D. S.; Klein, G. N.; Taylor, G. N.; Boeckman, Jr., R. K.; Medwid, J. B. Org. Synth., Coll. Vol. 1988, 6, 101.
- 38 Stowell, J. C.; Keith, D. R.; King, B. T. Org. Synth. 1984, 62, 140.
