Preparation and Application of 2-Bromo-5-hydroxybenzoic Acid

The molecular formula of 2-bromo-5-hydroxybenzoic acid is C7H5BrO3 and it appears as a white powder. Regarding this substance, some physical properties are as follows: density: 1.861g/cm3; Boiling point: 374.5 ℃ at 760 mmHg; Flash point: 180.3 ℃; Refractive index: 1.654.

Preparation method

The preparation method of 2-bromo-5-hydroxybenzoic acid includes the following steps: 1) Mix 2-bromo-5-fluorotoluene with organic solvent and alkaline solution in proportion, and heat to 65-85 ℃; 2) Add potassium permanganate in batches and react at a temperature of 85-105 ℃ for 0.5-4 hours until the reaction of 2-bromo-5-fluorotoluene is complete; 3) The reaction solution was cooled to room temperature, filtered, and the filter cake was washed with water. The filtrate was collected and concentrated under reduced pressure to recover the solvent. The residue was 2-bromo-5-fluorobenzoate; 4) Mix 2-bromo-5-fluorobenzoic acid salt with water, heat to 90-130 ℃, and react for 3-9 hours until the reaction of 2-bromo-5-fluorobenzoic acid is complete; 5) The reaction solution was cooled to room temperature, adjusted to pH 2-3, filtered, and the filter cake was washed with water. The solid was collected and dried to obtain the product 2-bromo-5-hydroxybenzoic acid. This method involves two steps of oxidation and hydrolysis to synthesize 2-bromo-5-hydroxybenzoic acid with high yield, high specificity, and selectivity, which is suitable for industrial production.

application

Urolithin A has antioxidant, anti-inflammatory, anti-tumor, anti-cancer and other effects. The research of Dr. Nicola Vannini's team [2] shows that the results of the research show that the food supplement of urolithin A can not only restore the hematopoietic function of aging hematopoietic stem cells, but also improve the immunity, which is expected to prevent infectious diseases and tumors. The current reported synthesis method of urolithin A has certain shortcomings, so further research is needed to develop efficient and simple synthesis methods. Based on a comprehensive examination of factors such as raw material cost and reaction yield, select a suitable synthesis route and optimize the key step (cyclization reaction). It was found that when the molar ratio of 2-bromo-5-hydroxybenzoic acid to resorcinol was 6:1, the mass fraction of NaOH solution was 5%, and the mass fraction of CuSO4 solution was 15%, the cyclization reaction was effectively carried out, and the target product urea A was obtained with an 86% yield.

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