Hydrochloric Acid → 3-(2,2,2-Trifluoroethoxymethyl)benzofuran-2-carboxylic acid

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Reaction Steps

To a suspension of sodium hydride (15 mg, 0.56 mmol) in anhydrous DMF (3 ml) was added 2,2,2-trifluoroethanol (270 μL, 3.7 mmol). The reaction mixture was stirred for 15-20 min and methyl 3-bromomethylbenzofuran-2-carboxylate (prepared as described in Reference C below) was added. Stirring was continued for 8 h, 1N aqueous NaOH was added and the reaction mixture was stirred for additional 10-15 min. The reaction mixture was acidified with 3M aqueous HCl to pH 3 and the product was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo to give crude 3-(2,2,2-trifluoroethoxymethyl)benzofuran-2-carboxylic acid (38 mg, 0.139 mmol), which was used without further purification.

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