Sodium Thiosulfate → HCID 86690465, compound

To an ice-cold solution of 2-bromo-3-fluoro-6-picoline (1.00 g) in chloroform (25 mL) was added 3-chloroperoxybenzoic acid (1.77 g), and the mixture was stirred while warming to room temperature for 22 hr. After cooling in ice again, additional 3-chloroperoxybenzoic acid (590 mg) was added and the mixture was stirred while warming to room temperature for 21 hr. An aqueous sodium thiosulfate solution was added to the reaction mixture, and the resulting mixture was then stirred. Thereafter, saturated aqueous sodium hydrogen carbonate solution and water were added thereto, followed by extraction with chloroform. The organic phase was washed with brine, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=98:2-0:100) to afford 2-bromo-3-fluoro-6-methylpyridine 1-oxide (604 mg).

1. temperatureAfter cooling in ice again
2. stirringthe mixture was stirred
3. temperaturewhile warming to room temperature for 21 hr
4. stirringthe resulting mixture was then stirred
5. extractionfollowed by extraction with chloroform
6. washThe organic phase was washed with brine
7. distillationthe solvent was then distilled off under reduced pressure
8. customThe resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=98:2-0:100)

ORD record

ord-a86a9c06001d48f19f531d6c90a32c91

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729271B2