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To a solution of <strong>[10242-08-7]5-methoxybenzofuran-2-carboxylic acid</strong> (5.04 g, 26.2 mmol) in methanol (50 mL) was added thionyl chloride (2.3 mL, 32 mmol) dropwise at 0 0C. After stirring for 72 h at room temperature, the reaction mixture was poured into water (150 mL) and filtered to provide white solids. The white solids were dissolved in toluene (100 mL) and washed with 1 M aqueous NaHCO3, brine, and dried over magnesium sulfate. Concentration in vacuo provided crude S-methoxybenzofuran^-carboxylic acid methyl ester (5.15 g, 95%) as a white solid, which was used without further purification.
95%
With thionyl chloride; at 0 - 20℃; for 72h;
Reference C; Synthesis of 5-(tetrahydro-4H pyran-4-yloxy)-benzofuran-2-carboxylic acid; Step 1; To a solution of <strong>[10242-08-7]5-methoxybenzofuran-2-carboxylic acid</strong> (5.04g, 26.2 mmol) in MeOH (50 mL) was added thionyl chloride (2.3 mL, 32 mmol) dropwise at 0 C. After 72 hr of stirring at room temperature, the reaction mixture was poured into H20 (150 mL) and filtered to provide white solids. The white solids were dissolved in toluene (100 mL) and washed with 1 M NaHCO3 (aq), and dried over MgS04. Upon drying in vacuo, 5-methoxybenzofuran- 2-carboxylic acid methyl ester (5.15 g, 95%) was obtained as a white solid.
With thionyl chloride; at 20℃; for 72h;
5-Methoxybenzofuran-2-carboxylic acid (5.04 g, 26 mmol) was weighed into a 200 ml round bottom flask fitted with a stir bar, septum and nitrogen inlet. Anhydrous MEOH (50 ml) was added under nitrogen atmosphere. The solution was cooled in an ice bath and thionyl chloride (2.3 ML, 32 mmol) was added dropwise with vigorous stirring. After stirring for 72 h at room temperature, the reaction mixture was poured into water (150 ML) and the white solid was collected. The solid was dissolved in toluene (100 ml) and the solution was washed with 1 M NaHC03 and brine and dried over MGS04. Removal of the organic layer provided 5-methoxybenofuran-2-carboxylic acid methyl ester as a white solid (5.15 g).
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