2-Fluoroaniline → HCID 59026788, compound

Participants

Reaction Steps

Lithium bis(trimethylsilyl)amide (54.6 mL, 1.0 M in THF, 54.6 mmol) was added to a solution of 2-fluoro aniline (3.5 mL, 36.4 mmol) in THF (100 mL) at −78° C. The resulting solution was for 1 h at −78° C. 3-Bromo-5-fluoro-isonicotinic acid (1) (4.0 g, 18.2 mmol) was added as a solid, and the reaction solution was stirred for 48 h at room temperature. The reaction solution was concentrated via rotary evaporation, diluted with satd. NaHCO3, and washed with EtOAc. The aqueous solution was acidified with concentrated HCl. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to afford the desired product (4.2 g, 74%) as a yellow solid.

Provenance & Evidence