background and overview[1][2]
the chinese alias of 5-bromo-2-hydroxy-3-methoxybenzaldehyde is 5-bromo-o-vanillin, cas number 5034-74-2, chemical formula c8h 7bro3. molecular weight 231.04300, brown powder, density 1.653g/cm3, melting point 125-127 °c (lit.), boiling point 277.2ºc at 760mmhg, flash point 121.4ºc, refractive index 1.622. 5-bromo-2-hydroxy-3-methoxybenzaldehyde is a pharmaceutical intermediate for preparing drugs.
preparation [1]
the preparation method of 5-bromo-2-hydroxy-3-methoxybenzaldehyde can use glacial acetic acid as the solvent, o-vanillin, liquid bromine, and potassium bromide as raw materials to synthesize 5-bromo-o- vanillin. the orthogonal test method was used to investigate the factors affecting the yield. the optimal conditions are: the reaction temperature is 100°c, the dropwise addition time of liquid bromine is 50min, and the reaction time is 90min. under these conditions, the product yield was 92.5%.
the specific steps are as follows: add o-vanillin (16 g) to a 1 l round-bottomed flask, then add glacial acetic acid (80 g), potassium bromide (25 g) and 40 ml water, and heat the reaction solution to 100°c, then dropwise add liquid bromine (17.5 g), complete the addition in 50 minutes, react at 100°c for 90 minutes, cool to 70°c, evaporate most of the solvent under reduced pressure, then add 1l of water, cool to 0～5℃, incubate for 2 h, centrifuge to separate the product, wash the product with 2×10 ml water, and vacuum dry for 21 h, yield: 14.8g (92.5%).
apply[2]
5-bromo-2-hydroxy-3-methoxybenzaldehyde is a pharmaceutical intermediate for preparing drugs. if some research discloses a mixed copper-based compound. the structural formula of the mixed copper-based complex is [cu(c10h10no5sbr)(c 12h8n2)]·ch3oh, where [cu(c10 h10no5sbr)(c12h8n2)] is the coordination unit, cu(c10h10no5sbr is the schiff base anion ligand, c12h8n2 is the neutral ligand 1,10′-phenanthroline.
preparation method: first mix taurine and strong alkali, add organic solvent, stir and dissolve, then add 5-bromo-2-hydroxy-3-methoxybenzaldehyde, the taurine, strong alkali and the molar ratio of 5-bromo-2-hydroxy-3-methoxybenzaldehyde is 1~2:2~3:1~2, stir at constant temperature for 2~4h, stop the reaction, and obtain the potassium salt of the ligand k 2c10h10no5sbr; then add the potassium salt of the ligand k2 mix c10h10no5sbr and copper salt, dissolve it in a mixed solvent of methanol/water, and then add 1,10′-o phylophenanthroline reacts at a constant temperature for 8 to 20 hours. after the reaction is completed, a mixed copper-based complex is obtained. the mixed copper-based compound is not only a candidate for anti-tumor drugs, but also a good inhibitor of tumor angiogenesis, and is a candidate for a new type of bifunctional anti-tumor drugs.
main reference materials
[1] research on the synthesis process of 5-bromo-2-hydroxy-3-methoxybenzaldehyde
[2] cn201810253423.2 a mixed copper-based complex and its preparation method and application
