2-Fluorobenzoic acid → HCID 86594893, compound

Participants

Reaction Conditions

Reaction Steps

To a cold solution of 4-[2-(4-chloro-3-trifluoromethylphenyl)ethyl]-benzenamine (4.33 g, 14.45 mmol) in THF (50 mL) at −78° C., was added LHMDS (43.35 mL, 43.35 mmol) (1M/THF) dropwise. Allowed the reaction mixture to stir for 10 minutes at −78° C. A solution of 2-fluorobenzoic acid (2.02 g, 14.45 mmol) in THF (50 mL) was added dropwise. The mixture was stirred for 2 hours at −78° C., then warmed to room temperature and let stir for additional 3 hours. The reaction mixture was concentrated in vacuo (40° C.) to remove the organic solvent. This residue was acidified to pH 3 with 3N HCl (aq.). This precipitate was collected by filtration, rinsed with 10% HCl (40 mL), and dried in vacuum for overnight to give as a pale solid, 4.3 g (10.24 mmol, 70%) of the desired product. mp 150-152° C.

Provenance & Evidence