Schuisky, Peter; Federsel, Hans-Jurgen; Tian, Wei published the artcile< Regioisomerism in the Synthesis of a Chiral Aminotetralin Drug Compound: Unraveling Mechanistic Details and Diastereomer-Specific In-Depth NMR Investigations>, Recommanded Product: 2-(4-Bromo-3-methylphenyl)acetic acid, the main research area is regioisomerism synthesis chiral aminotetralin drug ARA2 unraveling mechanism.
During chem. process development of a novel 2-aminotetralin derivative(I) intended for use as an antidepressant, scrutiny of the byproduct present in the drug mol. revealed a set of regioisomers. Detailed studies showed that this impurity issue originated from an early synthetic step in which a brominated tetralone motif was generated in a ring-closing protocol. It was found that this reaction was accompanied by a migration of the aromatic bromo substituent via different bromonium species along two discrete pathways. This example of the halogen dance reaction resulted in the formation of a series of tetralone impurities with a bromine distributed across all available aromatic positions of the tetralin nucleus. Subsequently, when subjected to reductive amination conditions, each of these tetralones gave rise to pairs of aminotetralins in a diastereomeric relationship. NMR investigations revealed that the alicyclic portion of the compounds thus formed displayed very complex signal patterns, which required further in-depth studies using a variety of sophisticated techniques. As a result, a deep insight into the structural features of the current 2-aminotetralin family was obtained, which is emphasized by the definition of a novel “”0.2 ppm rule”” allowing the absolute configuration at tetralin C-2 to be determined
Journal of Organic Chemistry published new progress about Absolute configuration. 215949-57-8 belongs to class bromides-buliding-blocks, and the molecular formula is C9H9BrO2, Recommanded Product: 2-(4-Bromo-3-methylphenyl)acetic acid.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary