Extracurricular laboratory: Synthetic route of 109-04-6

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109-04-6, 2-Bromopyridine, and friends who are interested can also refer to it.

109-04-6, 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. 109-04-6, name is 2-Bromopyridine. A new synthetic method of this compound is introduced below.

To a -40 C solution of 2.5 M n-BuLi (18 mL) in THF (300 mL) is added 2- bromopyridine (5.0 g, 32 mmol) over 15 min. The reaction is stirred for 1 h at -40 C, and then treated with 2-Amino-5-bromo-benzoic acid (6.9 g, 32 mmol) in THF (300 mL). The reaction is warmed to 0 C and stirred for 2 h then quenched with TMSC1 (3.4 g, 32 mmol). The reaction is stirred at room temperature for 30 min then cooled to 0 C and quenched with 3M HCl (20 mL). The aqueous layer is separated and the organic layer is extracted with 3M HCl. The organic layer is basified with solid NaOH, the resulting mixture is extracted with EtOAc, and the organic layer is dried over Na2S04, filtered and concentrated. The residue is purified by column chromatography on silica gel to give the desired product as a yellow solid. Yield: 5.50 g (62.7%) HPLC-MS: M+H=277/279; tRet =3.16 min; AM6

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109-04-6, 2-Bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; SMETHURST, Christian; ENGELHARDT, Harald; GIANNI, Davide; REISER, Ulrich; WO2014/154762; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem