By Desmurs J.-R., Gerard B., Goldstein M.J.
The natural molecules which are used, fairly within the parts of pharmacy and agrochemicals, have gotten an increasing number of complicated either of their chemical nature and spacial configuration. a fancy molecular constitution is necessarily fragile; it can't be produced less than critical stipulations (in specific excessive strain and temperature). additionally there's a challenge of the scale-up of a product from the laboratory to the commercial scale. The keep an eye on of the reactivity, selectivity, and yield and using sufficiently light commercial stipulations are all components that has to be taken into consideration via commercial chemists. among the ''tools'' giving controllable reactivity, selectivity, and comparatively light response stipulations is bromine. The natural chemistry of bromine occasionally offers fabulous selectivities in comparison to these of chlorine. This quantity that's in response to ''Orgabrom '93'', brings jointly the most contributions provided at this occasion.
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Additional info for Advances in Organobromine Chemistry II: Proceedings Orgabrom '93, Jerusalem, June 28-July 2, 1993
17. 28 BROMINATION AND OXIDATION AMMONIUM TRIBROMIDE WITH BENZYLTRIMETHYL- SHOJI KAJIGAESHI a) AND TAKAAKI KAKINAMI b) a) Department of Applied Chemistry and Chemical Engineering, Faculty of Engineering, Yamaguchi University, Ube 755, Japan b) Department of Chemical and Biological Engineering, Ube Technical College, Ube 755, Japan ABSTRACT Our recent studies on effective bromination and oxidation using benzyltrimethylammonium tribromide (BTMA Br3), stable solid, are described. Those involve electrophilic bromination of aromatic compounds such as phenols, aromatic amines, aromatic ethers, acetanilides, arenes, and thiophene, czbromination of arenes and acetophenones, and also bromo-addition to alkenes by the use of BTMA Br 3.
For instance, reactions of phenol with 1 equiv, of TBA Br3 gave 4-bromophenol, and with 2 equiv, of BTMA Br 3 gave 2,4-dibromophenol; furthermore, reactions with 3 equiv, of BTMA Br3 gave 2,4,6-tribromophenol in good yields, respectively (ref. 6). n TBA Br 3 or n B T M A Br 3 ~-"N~R HO CH2C12-CH3OH, rt. 0 . 5 - 1 h Br n 84-93 % Fig. 4. Bromination of Phenols with TBA Br 3 or BTMA Br 3 Because the presence of methanol markedly facilitates the bromination of phenols, we decided that the active species is probably methyl hypobromite produced by the reaction of these tribromides with methanol as shown below (Fig.
S. Kajigaeshi, Y. Morikawa, S. Fujisaki, T. Kakinami, K. Nishihira, Bull. Chem. Soc. , 64, 336 (1991). 34. S. Kajigaeshi, Y. Morikawa, S. Fujisaki, T. Kakinami, K. Nishihira, Bull. Chem. Soc. , 64, 1060 (1991). 35. A. Nishida, N. Kohro, S. Fujisaki, S. Kajigaeshi, Tech. Rep. , 4, 309 (1991). 36. S. Kajigaeshi, K. Murakawa, S. Fujisaki, T. Kakinami, Bull. Chem. Soc. , 62, 3376 (1989). 37. S. Kajigaeshi, K. Murakawa, S. Fujisaki, T. Kakinami, Chem. Express, 6, 129 (1991). 38. S. Kajigaeshi, T. Kakinami, T.