m-Chloroperbenzoic acid → 3-Bromo-2-methylpyridine N-oxide

Temperature

0 °C

To a solution of 3-bromo-2-methylpyridine (5 g, 29.1 mmol) in DCM (50 ml) was added portionwise at 0° C. m-chloroperbenzoic acid (70%, 8.6 g, 34.9 mmol). The solution was stirred at 0° C. for three hours and then at room temperature overnight. The mixture was filtered, the residue was washed with DCM and the combined DCM phases were quenched with a 10% solution of sodium thiosulfate. The phases were separated, the organic phase was washed with a saturated solution of sodium bicarbonate and brine, dried (sodium sulfate) and concentrated under reduced pressure. The residue was purified by column chromatography (silica, diethyl ether, then DCM/methanol 95:5) to yield 4.44 g (23.6 mmol, yield 81%) MS (multi-mode) m/z=190.0 [M+1]+.

1. customat room temperature
2. customovernight
3. filtrationThe mixture was filtered
4. washthe residue was washed with DCM
5. customthe combined DCM phases were quenched with a 10% solution of sodium thiosulfate
6. customThe phases were separated
7. washthe organic phase was washed with a saturated solution of sodium bicarbonate and brine
8. dry with materialdried (sodium sulfate)
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by column chromatography (silica, diethyl ether
11. customDCM/methanol 95:5) to yield 4.44 g (23.6 mmol, yield 81%)

ORD record

ord-9b821ed472494f36a9b360b4039bd2ee

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260441B2