Dimethylformamide → 2-Formyl-5-(trifluoromethyl)benzoic acid

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Reaction Conditions

Reaction Steps

To a 250 mL round-bottomed flask, was added 2.5 M n-butyllithium/hexane (8.92 mL, 22.30 mmol) in tetrahydrofuran (40 mL) and cooled to −78° C., followed by dropwise addition of 2-bromo-5-(trifluoromethyl)benzoic acid (3 g, 11.15 mmol) in tetrahydrofuran (20 mL). After 30 min N,N-dimethylformamide (0.978 g, 13.38 mmol) was added and the solution slowly allowed to warm to rt. To the reaction was added saturated ammonium chloride solution, followed by addition of saturated NaHCO3 solution until basic. The aqueous layer was separated, and 2 N HCl was added until acidic. The mixture was extracted with ethyl acetate (3×20 mL). The organic layers were combined, dried, filtered, and concentrated. The resulting solid was used without further purification. MS (DCI/NH3) m/z 512 (M+NH4)+.

Provenance & Evidence