m-Chloroperbenzoic acid → 2-Bromo-3-methylpyridine 1-oxide

A mixture of 2-bromo-3-methyl-pyridine (1000 mg, 5.81 mmol) and 3-chloroperoxybenzoic acid (2150 mg, 8.72 mmol) in dichloromethane (8 mL) was stirred overnight at room temperature. The reaction mixture was diluted with DCM (50 mL) and washed with saturated aqueous sodium thiosulfite (10 mL) followed by saturated aqueous sodium bicarbonate (10 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue that was purified by flash chromatography (4 g, Silica, 0-10% methanol in DCM). Desired fractions were combined and evaporated in vacuo to afford the title compound as white solid (851 mg, 78%), which was used in the next step without further purification.

1. washwashed with saturated aqueous sodium thiosulfite (10 mL)
2. customThe organic layer was separated
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto provide a residue that
7. customwas purified by flash chromatography (4 g, Silica, 0-10% methanol in DCM)
8. customevaporated in vacuo

ORD record

ord-a52f76a1d5724345b5ce7d4a00a9e79c

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08623889B2