Bromine → 2-Bromo-1-(2,3-dihydrobenzofuran-6-YL)ethan-1-one

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Reaction Steps

Br2 (0.36 ml, 7.01 mmol) was added dropwise to a stirring solution of 1-(2,3-dihydro-benzofuran-6-yl)-ethanone (1.13 g, 6.97 mmol) in MeOH (20 mL) held at 0° C. The reaction mixture was slowly allowed to reach room temperature. After 3 h, the reaction was quenched by the addition of NaHCO3 (aq, saturated)(until pH=8). Most of the methanol was removed under reduced pressure and the residue was extracted twice with EtOAc (2×20 mL). The organic extracts were pooled, washed with brine (10 mL), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by preparative HPLC using a gradient of 40-70% MeCN in a 0.1M ammonium acetate buffer as eluent. The fractions containing the desired product were pooled and most of the MeCN was removed under reduced pressure. The residue was extracted with EtOAc (2×20 mL) and the combined organic layers was washed with brine, dried over MgSO4 and concentrated. The obtained was finely washed MeOH to give the title compound.

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