Extracurricular laboratory: Synthetic route of C8H6BrNO

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 90110-98-8, name is 3-Bromo-4-(hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., Safety of 3-Bromo-4-(hydroxymethyl)benzonitrile

A solution of compound B (211 mg, 1.0 mmol) and triisopropyl borate (282 mg, 1.5 mmol) in anhydrous THF (10 mL) at N2 atmosphere was cooled to -78C. n- BuLi (0.9 mL, 2.25 mmol) was added dropwise at -78C. Then the mixture was allowed to warm to room temperature and stirr at room temperature for 1 h. The mixture was qunched with IN HCl and extracted with ethyl acetate (25 mL*3). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and concentrated under vacuum. The residue was purified by column chromatography (eluting with CH3OH and EtOAc =1 :1) on silica gel to give the desired compound C as a yellow solid (80 mg, 50 %).1H NMR (300 MHz, CDCl3): delta 9.50 (s, IH), 8.08 (s, IH), 7.83-7.92 (m, IH), 7.61-7.66 (m, IH), 5.06 (s, 2H). LC-MS: 160 (M + I)+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; JACOBS, Robert; ORR, Matthew; WRING, Stephen; CHEN, Daitao; ZHOU, Huchen; DING, Dazhong; FENG, Yiqing; YE, Long; HERNANDEZ, Vincent, S.; ZHANG, Yong-Kang; PLATTNER, Jacob J.; WO2010/45503; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts