Application of 5-bromo-2-hydroxy-3-methoxybenzaldehyde_Kain Industrial Additive

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