Hydrochloric Acid → HCID 56592442, compound

Participants

Reaction Steps

To a stirred solution of 5-chloro-4-(4-chloro-3-(trifluoromethyl)phenoxy)-2-fluorobenzoic acid (Preparation 32, 219 mg, 0.58 mmol) in DCM (3 mL) were added EDCl (167 mg, 0.87 mmol) and DMAP (106 mg, 0.87 mmol) and the reaction stirred at room temperature for 30 minutes. Methanesulfonamide (83 mg, 0.87 mmol) was added and the stirring continued at room temperature for 16 hours. DCM (25 mL) and 2M aq. HCl (5 mL) were added and the two layers separated. The organic extract was washed with 2M aq. HCl (5 mL) and brine (10 mL), dried (MgSO4), filtered and the solvent removed in vacuo. The crude material was purified by silica gel column chromatography eluting with EtOAc:heptane:AcOH (50:50:0.5), followed by recrystallisation from hot IPA to yield the title compound (89 mg, 34%) as a white solid.

Provenance & Evidence