Adding a certain compound to certain chemical reactions, such as: 20027-95-6, name is 1,5-Dibromo-2,6-dimethylnaphthalene, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 20027-95-6, category: bromides-buliding-blocks
(1) Synthesis of Intermediate C Intermediate C was synthesized according to the following scheme. In argon atmosphere, 17 g of 1,5-dibromo-2,7-dimethylnaphthalene, 35 g of bispinacolate diboron, 2.8 g of Pd(dppf)Cl2, 22 g of potassium acetate, and 400 ml of DMF were charged into a flask. The mixture was heated under stirring at 80 C for 65 h. After cooling, the precipitate was collected by filtration, washed with water and then toluene, and dried. Then, a mixture of 15 g of the obtained boronic ester, 27 g of bromoiodobenzene, 1.9 g of tetrakis(triphenylphosphine), 26 g of sodium carbonate, 120 ml of water, and 420 ml of DME in a flask was heated under stirring in argon atmosphere at 78 C for 665 h. After cooling, the precipitate was collected by filtration, washed with water and then methanol, and recrystallized from toluene. Then, a mixture of 13 g of the obtained dibrominated compound and 120 ml of pyridine in a flask was heated to 95 C. Thereafter, 10 g of potassium permanganate and 10 ml of ion exchanged water were added to the mixture. Then, 13 portions of 2 g of potassium permanganate and 2 ml of water were added to the mixture every ten minutes. The reaction product solution was hot-filtered and the filtrate was neutralized by a 2 N hydrochloric acid. The precipitated white solids were collected by filtration and washed with water. Finally, a mixture of 15 g of the obtained dicarboxylic compound and 300 ml of a concentrated sulfuric acid in a flask was heated under stirring at 85 C for 3 h. After cooling, the reaction product solution was slowly added to iced water, and the precipitated solids were collected by filtration and washed with ion exchanged water. The solids were further purified by sublimation, to obtain 7 g of the intermediate C. Through IR measurement of the obtained compound, it was found that the absorption attributable to carbonyl group appeared at 1720 cm-1. Mass spectrometric measurement showed a peak at M/Z = 802.
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Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2371812; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary