Indirect synthesis of bromo-substituted aromatic compounds was written by Kakinami, Takaaki;Yoneda, Takehiko;Yonemaru, Satoshi;Okamoto, Tsuyoshi;Kajigaeshi, Shoji. And the article was included in Ube Kogyo Koto Senmon Gakko Kenkyu Hokoku in 1991.Application In Synthesis of 2-Bromo-4-methyl-6-nitroaniline This article mentions the following:
The reaction of bromobenzenamine derivatives with NaNO2/H2SO4 in water and 30% phosphinic acid at 0-5° gave the bromo-substituted deamination products in fairly good yields. Bromination of benzeneamine gave 95% 2,4,6-tribromobenzenamine and deamination of the latter gave 97% 1,3,5-tribromobenzene. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-methyl-6-nitroaniline (cas: 827-24-7Application In Synthesis of 2-Bromo-4-methyl-6-nitroaniline).
2-Bromo-4-methyl-6-nitroaniline (cas: 827-24-7) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Application In Synthesis of 2-Bromo-4-methyl-6-nitroaniline
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary