m-Chloroperbenzoic acid → HCID 19010447, compound

Reaction equation

ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=1)[O:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.S([O-])(O)=O.[Na+]>C(Cl)Cl>[F:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=1)[O:16][C:17]1[CH:18]=[N+:19]([O-:9])[CH:20]=[CH:21][CH:22]=1

Participants

Procedure

To a solution of 46.3 g of m-chloroperbenzoic acid in 460 ml of methylene chloride, 37.35 g of 3-(3-fluorophenoxy)pyridine was added at room temperature, and the mixture was stirred at room temperature for 1.5 hours. An aqueous sodium hydrogen sulfite solution (20%, 120 ml) was added to the mixture and then the mixture was stirred for a few minutes. The organic layer separated was washed with 10% aqueous sodium hydroxide solution and with water, dried over anhydrous sodium sulfate, and concentrated. The residue was crystallized by trituration with isopropyl ether. The crystals were collected by filtration and washed with isopropyl ether to yield 34.44 g of pale yellow crystals, which were recrystallized from ethyl acetate to give colorless needles, mp 59°-61° C.