Synthesis
Step 1: Synthesis of methyl 2-(3-bromo-4-hydroxyphenyl)acetate
3-Bromo-4-hydroxyphenylacetic acid (0.3 g, 1.3 mmol, 1.0 equiv) and concentrated H2SO4 (2.77 μL, 0.05 mmol, 0.04 equiv) were dissolved in methanol (10 mL). The reaction mixture was stirred for 1 h at room temperature. Upon completion of the reaction, the reaction was quenched with NaOH solution and subsequently extracted with ethyl acetate (EtOAc). The organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: hexane/EtOAc = 5:1) to afford the target compound methyl 2-(3-bromo-4-hydroxyphenyl)acetate (0.2 g, 63% yield).LCMS m/z 245.0 [M + 1]+.
References
[1] Patent: WO2004/62661, 2004, A1. Location in patent: Page/Page column 28
[2] Patent: WO2010/138901, 2010, A1. Location in patent: Page/Page column 155
[3] Yakugaku Zasshi, 1933, vol. 53, p. 557,563; dtsch. Ref. S. 92
[4] Chem.Abstr., 1933, p. 4223
[5] Patent: WO2004/50637, 2004, A2. Location in patent: Page 74