Halogenation of Aromatic Compounds by N-Bromo- and N-Chlorosuccinimide under Ionic Conditions

Synthesis of microtubule-interfering halogenated noscapine analogs that perturb mitosis in cancer cells followed by cell death

“…However, reactions using NBS in the presence of H 2 SO 4 , FeCl 3 , and ZnCl 2 resulted in unsatisfactory yields (21-61%) together with the polysubstituted products. In another report by Lambert et al, aromatic substituted derivatives were obtained in good yields with NBS in 50% aqueous H 2 SO 4 [31], however, this method required considerably high acidic conditions which are not suitable for acid labile compounds, such as noscapine. Thus, there still exists a need to develop selective, reproducible and efficient procedures for the halogenation of such labile aromatic compounds that eliminate the limitations associated with the above discussed synthetic methods and offer quantitative yields of the desired compounds.…”

Regioselective and High-Yielding Bromination of Phenols and Anilins Using N-Bromosaccharin and Amberlyst-15

“…Aniline was immediately brominated at the para and ortho-positions with 1:1 ratio (Table 3, entry 15). Substituted anilines converted immediately to the corresponding mono-brominated products with excellent yields (Table 3, entries [16][17][18][19][20][21][22][23].…”

“…Also NBS-H 2 SO 4 -H 2 O system has been reported for the bromination of benzene and toluene. 20 This method is unsuitable for industrial bromination of aromatic compounds due to need for stoichiometric amount of catalyst during the reaction.…”

Environmentally Benign Electrophilic Halogenation of Naphthalenes by H<sub>2</sub>O<sub>2</sub>—Alkali Metal Halides in An Aqueous Cationic Micellar Media

“…In H 2 O 2 -HBr, the classical direct brominetion of aromatic compounds [54], HBr is highly toxic, corrosive and as harmful as of molecular bromine to the environment. Also NBS-H 2 SO 4 -H 2 O system has been reported for the bromination of benzene and toluene [55].…”