Uses
methyl 5-bromo-2,3-dihydroxybenzoate is used in the preparation of hydroxyalbuterol and bisubstrate inhibitors. Displays low inhibitory activity towards sn-glycerol-3-phosphate oxidase of Trypanosoma brucei brucei.
Synthesis
General procedure for the synthesis of methyl 5-bromo-2,3-dihydroxybenzoate from methanol and 5-bromo-2,3-dihydroxybenzoic acid: firstly, thionyl chloride (0.35 mL, 4.8 mmol) was mixed with methanol (5.4 mL) and stirred at room temperature for 30 min. Subsequently, 5-bromo-2,3-dihydroxybenzoic acid (600 mg, 2.57 mmol) was added to the mixture. The reaction mixture was continued to be stirred at room temperature for 2 hours and then heated to reflux for 7 hours. After completion of the reaction, the mixture was cooled and concentrated to give a brown solid. Finally, purification by column chromatography (using a 2.5 cm × 25 cm column with an eluent ratio of 1:4 ethyl acetate/hexane, which was subsequently adjusted to 1:1 ethyl acetate/hexane) afforded the target product methyl 5-bromo-2,3-dihydroxybenzoate (500 mg, 78% yield).
References
[1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 19, p. 2279 - 2280
[2] Patent: US2003/225091, 2003, A1. Location in patent: Page 63
[3] Patent: US2005/137162, 2005, A1. Location in patent: Page/Page column 6
[4] Chemistry - A European Journal, 2011, vol. 17, # 23, p. 6369 - 6381
[5] Patent: EP3404033, 2018, A1. Location in patent: Paragraph 0143-0144
