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ChemicalBook CAS DataBase List 5-BROMO-2-CHLORO-4-METHOXYPYRIDINE
880870-13-3

5-BROMO-2-CHLORO-4-METHOXYPYRIDINE synthesis

2synthesis methods
-

Yield: 45%

Reaction Conditions:

with N-Bromosuccinimide;sulfuric acid at 0 - 55; for 3 h;

Steps:

8.8
2-Chloro-4-methoxypyridine (13.3 g, 92.6 mmol) was dissolved in concentrated sulfuric acid (65 ml), N-bromosuccinimide (16.5 g, 92.6 mmol) was added under ice-cooling, and the mixture was stirred with heating at 55° C. for 3 hr. The reaction mixture was poured into ice water, alkalified with 8N aqueous sodium hydroxide solution, and extracted with chloroform. The organic layer was washed with saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1 to 5:1) to give the object product as a white solid (9.3 g, yield 45%). 1H NMR(CDCl3 300 MHz) (δ) ppm: 3.97 (3H, s), 6.84 (1H, s), 8.34 (1H, s)

References:

Satoh, Motohide;Aramaki, Hisateru;Nakamura, Hiroshi;Inoue, Masafumi;Kawakami, Hiroshi;Shinkai, Hisashi;Matsuzaki, Yuji;Yamataka, Kazunobu US2006/84665, 2006, A1 Location in patent:Page/Page column 49

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