Synthesis of 9,10-dihydroanthracen-9,10-imines was written by Anderson, Paul S.;Christy, Marcia E.;Colton, C. Dylion;Halczenko, Wasyl;Ponticello, Gerald S.;Shepard, Kenneth L.. And the article was included in Journal of Organic Chemistry in 1979.Reference of 452-62-0 This article mentions the following:
The cycloaddition of benzynes with isoindoles to generate the 9,10-dihydroanthracen-9,10-imine system (I) was examined in detail. A versatile synthesis of these ring-strained heterocycles based on a detailed anal. of the 2,3-dihydro-1H-isoindol-1-one (phthalimidine) approach to the prerequisite isoindoles is presented. A variety of synthetic methods to phthalimidines were evaluated and developed including: reductive amination of o-acylbenzoic acids; amidoalkylation of benzoic acids; halogenation and amination of o-alkylbenzoic acids; and reduction of phthalimides. In addition, generation of benzynes from chlorobenzenes and Li tetramethylpiperidide greatly increase the scope of the Diels-Alder reaction to form the desired products. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-fluorotoluene (cas: 452-62-0Reference of 452-62-0).
3-Bromo-4-fluorotoluene (cas: 452-62-0) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Reference of 452-62-0
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary