36255-23-9Relevant academic research and scientific papers
Graphene Oxide Promoted Oxidative Bromination of Anilines and Phenols in Water
Ghorpade, Prashant Vasantrao,Pethsangave, Dattatray Appasha,Some, Surajit,Shankarling, Ganapati Subray
, p. 7388 - 7397 (2018/07/29)
The mildly acidic and oxidative nature of graphene oxide, with its large surface area available for catalytic activity, has been explored in aromatic nuclear bromination chemistry for the first time. The versatile catalytic activity of graphene oxide (GO) has been used to selectively and rapidly brominate anilines and phenols in water. The best results were obtained at ambient temperatures using molecular bromine in a protocol promoted by oxidative bromination catalyzed by GO; these transformations proceeded with 100% atom economy with respect to bromine and high selectivities for the tribromoanilines and -phenols. Reduced graphene oxide (r-GO) was observed to form after the second recycle (third use) of GO. This technique is also effective with N-bromosuccinimide (NBS) as the brominating reagent. In the case of NBS, reactions were instantaneous and the GO displayed excellent recyclability without any loss of activity over several cycles.
An intriguing effect of lithium perchlorate dispersed on silica gel in the bromination of aromatic compounds by N-bromosuccinimide
Bagheri, Mojtaba,Azizi, Najmedin,Saidi, Mohammad R.
, p. 146 - 149 (2007/10/03)
A convenient and efficient procedure for electrophilic aromatic bromination has been developed by mixing of N-bromosuccinimide and an aromatic compound at room temperature on the surface of silica gel mixed with solid anhydrous LiClO4. All of the substrates examined underwent clean electrophilic aromatic bromination in reaction times of a few minutes to afford the corresponding bromoarenes under neutral conditions in excellent yield. In the case of thiophenol, no substitution reaction occurred, and the corresponding disulfide was obtained in excellent yield.
Synthesis of 2,6-disubstituted and 2,3,6-trisubstituted anilines
Pews,Hunter,Wehrmeyer
, p. 4809 - 4820 (2007/10/02)
A number of 2,6-disubstituted and 2,3,6-trisubstituted anilines have been prepared via the selective para dehalogenation of the corresponding anilines. Modification of the substituents on the amino nitrogen demonstrates that the selectivity is derived from steric rather than electronic effects. The effects of the choice of formate hydrogen donor, Pd catalyst, solvent, and temperature upon the efficiency and selectivity of the dehalogenation are discussed.
Halogenation Using Quaternary Ammonium Polyhalides. VI. Bromination of Aromatic Amines by Use of Benzyltrimethylammonium Tribromide
Kajigaeshi, Shoji,Kakinami, Takaaki,Inoue, Kazuhisa,Kondo, Manabu,Nakamura, Hiroko,et al.
, p. 597 - 599 (2007/10/02)
The reaction of aromatic amines with benzyltrimethylammonium tribromide in dichloromethane-methanol containing calcium carbonate powder for 0.5 h at room temperature gave bromo-substituted aromatic amines in good yields.
POLYBROMINATED AROMATIC COMPOUNDS. III. SYNTHESIS OF BROMINE-SUBSTITUTED ANISOLES
Shishkin, V. N.,Tanaseichuk, B. S.,Lapin, K. K.,Ivkina, A. A.,Butin, K. P.
, p. 2357 - 2366 (2007/10/02)
Reliable methods were developed for the synthesis of di-, tri-, and tetrabromoanisoles, and all the possible individual isomers were synthesized.The structures of the isomers were proved by alternative synthesis and spectral methods (PMR, IR).It was shown that the published data are incorrect in a number of cases; either the final product was assigned the incorrect structure, or the published methods led to mixture of the various isomers.
