Synthetic Route of 35450-36-3, A common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, molecular formula is C9H9BrO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Add CuI (19.45 mg), PdCl2 (PPh3) 2 (105.29 mg) to the round bottom flask,Under nitrogen, methyl 2-bromo-5-methoxybenzoate (1.68 mL), phenylacetylene (0.66 mL), Et3N (2.08 mL), and THF (15 mL) were added in this order, and the reaction was performed at 55 C for 6 h.TLC tracks the progress of the reaction; after the reaction is complete, the resulting reaction solution is cooled to room temperature,Then filtered through diatomaceous earth and purified by column chromatography to obtain the first intermediate;Dissolving the first intermediate in methanol, adding a 10% NaOH solution, and stirring at room temperature for 2 h,TLC tracks the progress of the reaction; after the reaction is complete, adjust the pH of the resulting reaction solution to dilute 2-3 with dilute hydrochloric acid,The obtained solid was filtered and purified by recrystallization to obtain a second intermediate;Add SOCl2 to the second intermediate and reflux at 90 C for 2 h.TLC followed the progress of the reaction; after the reaction was completed, SOCl2 was removed to obtain a third intermediate;At 0 C, add N-methoxyamine and potassium carbonate to 15 mL of ethyl acetate in this order.(EA) and water (EA: water volume ratio = 2: 1), the third intermediate was added dropwise after 10 min, and the reaction was performed at room temperature for 1 h.TLC tracks the progress of the reaction; after the reaction is complete, it is extracted with EA and H2O.Dry over anhydrous sodium sulfate and recrystallize to obtain N-methoxy-5-methoxy-2-phenylethynylbenzamide (1h);
The synthetic route of 35450-36-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Hunan University of Science and Technology; Xie Wenlin; Liu Renzhi; Qiu Guanyinsheng; (15 pag.)CN110590641; (2019); A;,
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