2-Bromothiazole → Methyl 3-bromo-5-(hydroxy(thiazol-2-yl)methyl)benzoate

Participants

Reaction Steps

To a stirred solution of 2-bromothiazole (0.40 g, 24.4 mmol) in THF (60 mL) under nitrogen at rt was added 2M isopropylmagnesium chloride solution in THF (10 mL, 20 mmol). The mixture was stirred at rt for 1 h and then cooled to 0° C. Methyl 3-bromo-5-formylbenzoate (1.0 g, 4.1 mmol) was added and the reaction mixture was stirred at 0° C. for 30 minutes. The reaction mixture was quenched with water (30 mL) and extracted with CH2Cl2 (60 mL×3). The combined organic layers were dried over anhydrous MgSO4 and concentrated. The residue was purified by flash chromatography to afford the title compound (0.90 g).

Provenance & Evidence