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

A mixture of 3-bromo-2-methylpyridine (0.14 mL, 1.2 mmol) and m-chloroperbenzoic acid (420 mg, 1.8 mmol) in methylene chloride (4 mL) was stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with saturated aqueous sodium bicarbonate solution (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 4 g, ISCO, 0-10% methanol in dichloromethane) to afford the title compound as a white solid (140 mg, 61%), which was used in the next step without further purification.

1. washwashed with saturated aqueous sodium bicarbonate solution (20 mL)
2. customThe organic layer was separated
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. customevaporated in vacuo
6. customto afford a residue that
7. customwas purified by flash chromatography (silica, 4 g, ISCO, 0-10% methanol in dichloromethane)

ORD record

ord-f91746b28a544c2ca326d59a2b6ac9ee

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206175B2