Triethylamine → Methyl 3-Cyano-4-(trifluoromethylsulfonyloxy)benzoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of crude methyl 3-cyano-4-hydroxybenzoate (2.50 g) from above and Et3N (1.31 g, 13.0 mmol) in anhydrous DCM (20 mL) was added Tf2O (1.82 g, 6.50 mmol) dropwise and then the reaction mixture was stirred at 30° C. for 2 hours. The resulting mixture was suspended in water (50 mL) and extracted with DCM (50 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE/EtOAc=10/1) to give Intermediate 1 (550 mg, 2-step yield: 28%) as a colorless oil. 1H NMR (CDCl3 300 MHz): δ 8.43 (d, J=2.1 Hz, 1H), 8.37 (dd, J=8.7, 2.1 Hz, 1H), 7.59 (d, J=8.7 Hz, 1H), 3.98 (s, 3H).

Provenance & Evidence