Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 73870-24-3, name is 4-(Bromomethyl)pyridine hydrobromide. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-(Bromomethyl)pyridine hydrobromide
Sodium hydride {3.0 g, 125 mmol, 10 eq. (5.0 g of 60%> NaH in oil)} was added to a solution of galeterone (1, 5.0 g, 12.9 mmoL, 1 eq.) in THF (80 mL) at 0C under argon atmosphere. A white precipitate formed and after stirring for one minute, DMF (5.0 mL) was added and the reaction mixture was allowed to stir for 10 minutes at room temperature. The reaction mixture was placed at 0C and lithium carbonate (5.0 g, 67.7 mmoL, 5 eq. ) was added, followed immediately by 4-(bromomethyl)pyridine hydrobromide (14, 10 g, 39.5 mmoL, 3 eq.) and the reaction mixture was allowed to stir at 0C for 30 minutes. The reaction mixture was removed from 0C and stirring continued at ambient temperature for 18 hours under argon atmosphere. The color of the reaction mixture changed from clear to dark red during the 18-hour period. After 18 hours, the reaction mixture was placed at 0C, water (30 mL) was added to quench unreacted NaH, and the mixture was stirred for 10 minute. Volatile (THF) were removed in vacuo and water (70 mL) was added to the residue aqueous phase. The aqueous phase was extracted with ethyl acetate (EtOAc) (150 mL x 3). Ethyl acetate extract was washed with brine (80 mL x 2), dried with anhydrous Na2SO4 and concentrated in vacuo to give a dark red crude product. Purification by flash chromatography using 3% MeOH/EtOAc as eluent afforded compound galeterone 3beta-pyridine methoxylate (3) as a white solid (3.78 g, 7.88 mmoL, 61%), mp 177-179C. Rf= 0.31 (5% MeOH/EtOAc).
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Reference:
Patent; UNIVERSITY OF MARYLAND, BALTIMORE; NJAR, Vincent C.O.; PURUSHOTTAMACHAR, Puranik; MURIGI, Francis; (33 pag.)WO2017/223320; (2017); A1;,
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