Selective halogen-lithium exchange in bromophenylalkyl halides was written by Parham, William E.;Jones, Lawrence D.;Sayed, Yousry A.. And the article was included in Journal of Organic Chemistry in 1976.Reference of 5388-42-1 This article mentions the following:
Exchange of the aryl halide atom in o-BrC6H4CH2Cl, o-BrC6H4(CH2)2Br, and o-BrC6H4(CH2)3Cl for Li was carried out with BuLi in THF-hexane at -100掳. The stable lithio derivatives reacted with a variety of electrophiles; e.g., o-LiC6H4CH2Cl (I) with H2O, cyclohexanone, or PhNCO at low temperature gave, resp., PhCH2Cl, II, and III. I with H2O at room temperature gave 9,10-dihydroanthracene (not benzocyclopropene). Benzocyclobutene was formed from o-LiC6H4(CH2)2Br under similar conditions. O-halobenzyl bromides were lithiated at the benzyl bromine atom and underwent subsequent coupling to bibenzyl. O-BrC6H4(CH2)3Br with BuLi underwent intramol. coupling to indan. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).
2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Reference of 5388-42-1
Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles