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ChemicalBook CAS DataBase List 2-Chloro-4-Bromo-3-Picoline

2-Chloro-4-Bromo-3-Picoline synthesis

2synthesis methods
-

Yield: 97.2%

Reaction Conditions:

Stage #1:2-chloro-4-bromopyridine with lithium diisopropyl amide in tetrahydrofuran at -70; for 1 h;
Stage #2:methyl iodide in tetrahydrofuran at -70; for 0.833333 h;

Steps:

46.46a Step 46a: 4-bromo-2-chloro-3-methylpyridine (4-bromo-2-chloro-3-methylpyridine) (Compound 402-25) Preparation :
4-bromo-2-chloropyridine (5 g, 26.19 mmol, 1.0 eq.) was dissolved in 30 ml of dry tetrahydrofuran, and under conditions of -70 °C, slowly added dropwise a freshly prepared lithium diisopropylamide solution (50 ml, 28.8 mmol, 1.1 equiv.). Kept at -70 °C, after reaction for one hour, iodomethane (4.087 g, 28.8 mmol, 1.1 eq). After 50 minutes reaction at low temperature, quenched with saturated sodium bicarbonate solution, the reaction, extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, and concentrated to give a solid compound 4-bromo-2-chloro-3-methylpyridine (5.22 g, yield: 97.2%).

References:

Guangzhou Kaisheng Beite Pharmaceutical Co., Ltd.;Cai, Xiong;Qian, Changgeng;Liu, Bin;Li, Junqi;Lin, Mingsheng;Qing, Yuanhui;Weng, Yunwo;Wang, Yanyan;Xue, Weicai;You, Huajin;Zhou, Shiqing CN105622638, 2016, A Location in patent:Paragraph 0381

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