Some benzonorbornadiene derivatives was written by Tanida, Hiroshi;Muneyuki, Ryonosuke;Tsuji, Teruji. And the article was included in Bulletin of the Chemical Society of Japan in 1964.Computed Properties of C7H6BrF This article mentions the following:
The cycloaddition of substituted benzynes in the preparation of β-substituted benzonorbornadienes was described. The Wittig and Knauss procedure (CA 54, 505e) for preparation of benzynes was used. 4-Bromo-3-iodoanisole (I) (prepared from 6-bromo-m-anisidine) was used for the preparation of 4-methoxybenzyne. Racemic 4′-methoxybenzonorbornadiene was obtained in a 40% yield by the reaction of I with cyclopentadiene and Mg. 3-Bromo-4-fluorotoluene was prepared from 2-bromo-p-toluidine by the Schiemann reaction, and its cycloaddition to cyclopentadiene was carried out to give 54% 4′-methylbenzonorbornadiene (II). The benzyne reaction of 2-bromo-4-chlorofluorobenzene, obtained by the Schiemann reaction of 2-bromo-4-chloroaniline, proceeded with cyclopentadiene by the elimination of Br and F to give 55.6% 4′-chlorobenzonorbornadiene. The position of the substituents on the benzene nucleus of the benzonorbornadienes was determined by conversion into the 2-substituted naphthalenes through benzoyloxylation at the 7-position, hydrolysis, and Oppennauer oxidation The reaction of 3-bromo-4-iodobenzonitrile with Mg gave 3-bromobenzonitrile; no reaction occurred with Li. The reaction of 2,5-dibromoiodobenzene with Mg and cyclopentadiene gave a product containing 25.4% benzonorbornadiene, 28.6% p-dibromobenzene, 6.6% 3-bromoiodobenzene, 21.1% 4′-bromobenzonorbornadiene, and three unidentified products. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-fluorotoluene (cas: 452-62-0Computed Properties of C7H6BrF).
3-Bromo-4-fluorotoluene (cas: 452-62-0) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Computed Properties of C7H6BrF
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary