Potassium Fluoride → Methyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoate

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Reaction Steps

To a stirred mixture of methyl 3-bromo-5-formylbenzoate (0.60 g, 2.5 mmol), tetra-N-butylammonium bromide (0.90 g, 2.8 mol), potassium fluoride (10 mg, 0.17 mmol), and toluene (10 mL) at −20° C. was added (trifluoromethyl)trimethylsilane (0.74 mL, 5.0 mmol). The reaction mixture was stirred for 20 min, and then quenched with water. To the mixture were added 1 M HCl aqueous solution (2 mL) and 1,4-dioxane (12 mL), and the mixture was stirred for 30 min. The aqueous phase was extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by flash column to afford the title compound.

Provenance & Evidence