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 694-80-4 as follows. category: chlorides-buliding-blocks
General procedure: Step 1: The substituted bromobenzene (1 equiv) and (3-formylphenyl)boronic acid or (4-formylphenyl) boronic acid (1 equiv) were dissolved in a mixture of 1M sodium carbonate aqueous solution (15mL), EtOH (5mL) and toluene (15mL). After nitrogen substitution, Pd(PPh3)4 (0.05 equiv) was added. The reaction mixture was stirred at 80C under nitrogen atmosphere for 12h. The reaction mixture was cooled, and water (15mL) was added. The mixture was diluted with AcOEt (15mL), and the insoluble material was filtered off through Celite. The organic layer of the filtrate was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography using a mixture of petroleum ether/ethyl acetate (10:1, v/v) as eluent to afford the desired product 2a-r, 5a and 5b as a solid. Step 2: To a solution of 2a-r, 5a or 5b (1 equiv) in MeOH (10mL) and THF (20mL) was added portionwise sodium borohydride (3 equiv) at 0C and the mixture was stirred at 0C for 1h. The reaction mixture was pouring into ice water (10mL), and extracted with ethyl acetate (3×15mL), the organic fractions were combined, washed with saturated brine (2×15mL) prior to drying over anhydrous sodium sulfate. After filtration and concentrate using a rotary evaporator, the residue was used in next step without further purification. To a solution of the obtained solid (1 equiv) in dichloromethane (20mL) was slowly added thionyl chloride (6 equiv) and a catalytic amount of DMF at room temperature. After stirring at 40C for 4h, the reaction was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using a mixture of petroleum ether/ethyl acetate (20:1, v/v) as eluent to afford the desired product.
According to the analysis of related databases, 694-80-4, the application of this compound in the production field has become more and more popular.
Reference:
Article; Li, Zheng; Liu, Chunxia; Xu, Xue; Qiu, Qianqian; Su, Xin; Dai, Yuxuan; Yang, Jianyong; Li, Huilan; Shi, Wei; Liao, Chen; Pan, Miaobo; Huang, Wenlong; Qian, Hai; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 458 – 479;,
Chloride – Wikipedia,
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