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To a solution of (E)-methyl 3-(4-((2-bromo-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (2.4 g, 5.72 mmol) in DCM (20 mL) at room temperature was added BBr3 (1.0 M in Heptane, 17.17 mL, 17.17 mmol) dropwise. The resulting mixture was stirred at room temperature for 2 h after which time an aqueous buffer (pH 7.4, made from citric acid and dibasic sodium phosphate, 10 mL), cooled to 0° C. was slowly added into the reaction. The resulting mixture was then diluted with DCM (30 mL) and stirred at room temperature for 1 h. The phases were then separated and the organic phase was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude material was purified by column chromatography (SiO2, 0-100% EtOAc/Heptane) to afford (E)-methyl 3-(4-((2-bromo-6-hydroxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (1.6 g, 3.95 mmol, 69% yield) as a pale yellow solid and (E)-3-(4-((2-bromo-6-hydroxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylic acid (370 mg, 0.946 mmol, 17% yield) as a yellow solid.

1. additionwas slowly added into the reaction
2. customThe phases were then separated
3. dry with materialthe organic phase was dried over anhydrous Na2SO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe crude material was purified by column chromatography (SiO2, 0-100% EtOAc/Heptane)