Synthesis
Benzyl 2-benzyloxy-5-bromobenzoate (18 g, 45.3 mmol) was used as starting material and dissolved in methanol (50 mL). Subsequently, a solution of sodium hydroxide (7.25 g, 181 mmol) in water (20.00 mL) was added to this solution. The reaction mixture was heated to 60°C and the reaction was stirred at this temperature for 2 hours. Upon completion of the reaction, the solvent was removed by rotary evaporation. The residue was diluted with water and washed with ethyl acetate (EA). The aqueous layer was separated and acidified to pH=3 with 4N hydrochloric acid solution and subsequently extracted with ethyl acetate (EA). The organic phases were combined, washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. Finally, the target product 2-(benzyloxy)-5-bromobenzoic acid (13.46 g, 97% yield) was obtained by concentration under reduced pressure.LCMS analysis showed [M+H]+ m/z 307,309.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 2, p. 212 - 215
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 17, p. 4034 - 4038
[3] Patent: WO2011/38572, 2011, A1. Location in patent: Page/Page column 50
