Regioselective monobromination of aromatics via a halogen bond acceptor-donor interaction of catalytic thioamide and N-bromosuccinimide was written by Bovonsombat, Pakorn;Teecomegaet, Pattaradra;Kulvaranon, Panisanun;Pandey, Aditi;Chobtumskul, Kittithorn;Tungsirisurp, Sireethorn;Sophanpanichkul, Punyanuch;Losuwanakul, Satreerat;Soimaneewan, Dechathon;Kanjanwongpaisan, Patcharida;Siricharoensang, Pornpawit;Choosakoonkriang, Sirirat. And the article was included in Tetrahedron in 2017.Synthetic Route of C8H6Br2O2 This article mentions the following:
Regioselective monobromination of various aromatics was achieved at room temperature using N-bromosuccinimide and 5 mol% of thioamides in acetonitrile. With thiourea as catalyst, activated aromatics, such as anisole, acetanilide, benzamide and phenol analogs containing electron donating or withdrawing groups, were brominated with high regioselectivity. Room temperature brominations of weakly activated aromatics and deactivated 9-fluorenone were accomplished by 5 mol% thioacetamide, higher substrates concentrations and longer reaction times. A backbonding of the bromine lone pairs with the 锜?sup>*of C=S group and a halogen bond between the halogen bond donor bromine and the halogen bond acceptor sulfur of the thioamide are thought to be the principal interactions and cause of N-bromosuccinimide activation. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Synthetic Route of C8H6Br2O2).
3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. 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.Synthetic Route of C8H6Br2O2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary