m-Chloroperbenzoic acid → HCID 178517805, compound

Temperature

65 °C

3-chloroperoxybenzoic acid (21 g) was added to a dichloromethane (200 ml) solution of 2-chloro-3-fluoropyridine (10 g), and the obtained mixture was stirred at 65° C. for 8 hours. The reaction solution was cooled on ice. A saturated sodium thio sulfate aqueous solution was added to the reaction solution, and the obtained mixture was stirred for 20 minutes. A saturated sodium bicarbonate aqueous solution was added to the reaction solution, and the mixture was extracted with chloroform. The obtained organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was washed with t-butyl methyl ether/n-heptane (1/1), and the solid was collected by filtration. The obtained solid was dissolved in THF (150 ml). Triethylamine (13.2 ml) and trifluoroacetic acid anhydride (33.2 ml) were added to the solution, while the solution was stirred under cooling on ice. The obtained mixture was stirred at room temperature for 5 hours. A small amount of water was added to the reaction solution. Thereafter, a 5 N sodium hydroxide aqueous solution was added to the mixture, while the solution was stirred under cooling on ice. The obtained mixture was stirred at room temperature for 1 hour. The reaction solution was converted to the mild acidic range by addition of acetic acid, and it was then extracted with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride aqueous solution, then dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 1:1). The obtained solid was washed with t-butyl methyl ether/n-heptane (1/1) and then collected by filtration, so as to obtain the title compound (2.6 g).

1. temperatureThe reaction solution was cooled on ice
2. stirringthe obtained mixture was stirred for 20 minutes
3. extractionthe mixture was extracted with chloroform
4. dry with materialThe obtained organic layer was dried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. washThe residue was washed with t-butyl methyl ether/n-heptane (1/1)
7. filtrationthe solid was collected by filtration
8. dissolutionThe obtained solid was dissolved in THF (150 ml)
9. additionTriethylamine (13.2 ml) and trifluoroacetic acid anhydride (33.2 ml) were added to the solution, while the solution
10. stirringwas stirred
11. temperatureunder cooling on ice
12. stirringThe obtained mixture was stirred at room temperature for 5 hours
13. additionA small amount of water was added to the reaction solution
14. additionThereafter, a 5 N sodium hydroxide aqueous solution was added to the mixture, while the solution
15. stirringwas stirred
16. temperatureunder cooling on ice
17. stirringThe obtained mixture was stirred at room temperature for 1 hour
18. additionThe reaction solution was converted to the mild acidic range by addition of acetic acid, and it
19. extractionwas then extracted with ethyl acetate
20. washThe obtained organic layer was washed with a saturated sodium chloride aqueous solution
21. dry with materialdried over magnesium sulfate
22. concentrationconcentrated under reduced pressure
23. customThe obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 1:1)
24. washThe obtained solid was washed with t-butyl methyl ether/n-heptane (1/1)
25. filtrationcollected by filtration

ORD record

ord-2dc119711c0242e0a642d67f7d327b9a

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268848B2