4549-33-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 4549-33-1 as follows.
4-Picoline (2.0 mL, 21 mmol) was dissolved in THF (40 mL) under an argon atmosphere using a 150 mL Schlenk flask. The Schlenk flask was cooled down to-78C by using a dry ice/methanol cooling bath. A solution of n-butyllithium in hexane (12.0 mL, 18 mmol) was added to the solution by a syringe under an argon atmosphere. After the solution was stirred for 30 min, diethyl amine (2.2 mL, 22 mmol) was added to the solution by a syringe under an argon atmosphere. After the solution was stirred for 30 min, the solution was added to a solution of 1,9-dibromononane (20.0 mL, 99 mmol) in THF (10 mL) by a syringe under an argon atmosphere. The reaction mixture was gradually warmed to room temperature and stirred for 1 h. The solution was poured into 0.5M ammonium chloride (10 0mL) to quench the reaction at 0C. After evaporation of the organic solvent at 0C, the residual solution was dropped into 1M hydrobromic acid (100 mL), and the product was extracted with dichloromethane (4¡Á50 mL). The organic layers were combined, and dried with sodium sulfate (15 g). The organic layer was concentrated under reduced pressure. After the residual solution was dropped into hexane (200 mL), and then a pale yellow precipitate was formed. The pale yellow precipitate containing the product was recovered by centrifugation. The product 1 was obtained as a pale yellow powder (yield 5.12g, 65%). 1H NMR (500MHz, DMSO-d6): delta 8.42 (d, J=5.9Hz, 2H), 7.19 (d, J=5.9Hz, 2H), 3.50 (t, J=6.7Hz, 2H), 2.57 (t, J=7.6Hz, 2H), 1.81-1.72 (m, 2H), 1.61-1.52 (m, 2H), 1.39-1.20 (m, 12H).
According to the analysis of related databases, 1,9-Dibromononane, the application of this compound in the production field has become more and more popular.
Reference:
Article; Hashidzume, Akihito; Kuse, Akihiro; Oshikiri, Tomoya; Adachi, Seiji; Yamaguchi, Hiroyasu; Harada, Akira; Tetrahedron; vol. 73; 33; (2017); p. 4988 – 4993;,
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