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 2~4 hours, stop the reaction, and obtain the potassium salt K of the ligand 2C10H10NO5SBr; then add the potassium salt of the ligand K2 C10H10NO5SBr is mixed with copper salt, dissolved in a mixed solvent of methanol/water, and then 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
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