Synthetic Route of 1196157-14-8, 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. 1196157-14-8, name is 4-Bromo-5-methylpicolinaldehyde. A new synthetic method of this compound is introduced below.
To a solution of a 60% dispersion of NaH in mineral oil (0.29 g, 7.25 mmol) in DME (2 niL) at – 30 C was added a solution of ethyl 2-phosphonoacetate (1.46 mL, 7.29 mmol) in DME (13 mL), and the mixture was stirred at this temperature for 30 min. To this solution was added a solution of 4-bromo-5-methylpyridine-2-carbaldehyde (64) (1.32 g, 6.60 mmol) in DME (3 mL), and the reaction was stirred at -30 C for 1.5 h and then poured into water (50 mL) and extracted with ethyl acetate. The combined organic layers were washed with an aqueous saturated NH4CI solution and then brine, dried over sodium sulfate, filtered and concentrated in vacuo to give a crude product that was purified by column chromatography (150 mL Si02, ethyl acetate:hexanes 1 :9) to give 65 (1.553 g, 87%) as a colorless crystalline solid: ? NMR (400 MHz, CDCI3) ? 8.41 (s, 1H), 7.59 (d, J= 15.6, 1H), 7.58 (s, 1H), 6.88 (d, J= 15.6, 1H), 4.25 (q, J= 7.2, 2H), 2.38 (s, 3H), 1.31 (t, J= 7.2, 3H); 13C NMR (100.6 MHz, CDC13) ? 166.4, 151.6, 150.8, 141.6, 135.4, 134.7, 127.3, 122.9, 60.6, 19.4, 14.2.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,1196157-14-8, 4-Bromo-5-methylpicolinaldehyde, and friends who are interested can also refer to it.
Reference:
Patent; ARIZONA BOARD OF REGENTS, A BODY CORPORATE OF THE STATE OF ARIZONA ACTING FOR AND ON BEHALF OF ARIZONA STATE UNIVERSITY; WAGNER, Carl, E.; JURUTKA, Peter, W.; MARSHALL, Pamela, A.; WO2013/40227; (2013); A2;,
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