In 2017,Mi, Rui-Jie; Sun, Jing; Kuhn, Fritz E.; Zhou, Ming-Dong; Xu, Zhaoqing published 《A meta-selective-C-H alkenylation of phenol-derivatives employing a traceless organosilicon template》.Chemical Communications (Cambridge, United Kingdom) published the findings.Electric Literature of C8H6BrN The information in the text is summarized as follows:
A traceless O-benzeneacetonitrile silyl template-directed meta-selective-C-H Heck alkenylation of phenols was realized with good yields and high selectivities. Etherification of phenol with 3-cyanomethylphenylsilyl substituents gives the directing template, 3-R2C(CN)C6H4SiiPr2OC6H4R1 (R1 = Me, MeO, halo, CF3, MeO2C), which undergoes meta-regioselective palladium-catalyzed Heck alkenylation with Et acrylate, giving cinnamates 3-R2C(CN)C6H4SiiPr2OC6H3R1-3-CH:CHCO2Et; the latter can be easily deprotected, leaving hydroxycinnamates 3-HOC6H3R1CH:CHCO2Et. The template was readily removable through F–promoted O-Si cleavage under extremely mild conditions or recyclable through a p-TSA catalyzed process. The product was successfully applied in the preparation of a series of meta-alkenylated aromatic compounds In the experiment, the researchers used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Electric Literature of C8H6BrN)
According to other reports, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) is used in the preparation of diarylpyrimidines (DAPYs) as HIV-1 non-nucleoside reverse transcriptase inhibitors.Electric Literature of C8H6BrN
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts