m-Chloroperbenzoic acid → 2-Bromo-5-methylpyridine 1-oxide

Into a round-bottom flask, was placed a solution of 2-bromo-5-methylpyridine (10.0 g, 58.1 mmol, 1.00 equiv) in dichloromethane (250 mL). mCPBA (15.0 g, 86.9 mmol, 1.50 equiv) was added in several batches at room temperature. The resulting solution was stirred overnight at 30° C., then diluted with 50 mL of 2N sodium hydroxide (aq.). The pH value of the solution was adjusted to 10 with 2N sodium hydroxide (aq.). The aqueous phase was extracted with 3×100 mL of dichloromethane and the combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield 11.0 g (91%) of 2-bromo-5-methylpyridin-1-ium-1-olate as a yellow solid.

1. customInto a round-bottom flask, was placed
2. extractionThe aqueous phase was extracted with 3×100 mL of dichloromethane
3. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customto yield 11.0 g (91%) of 2-bromo-5-methylpyridin-1-ium-1-olate as a yellow solid

ORD record

ord-dd0389c101d74488b83f58d19e2af4bc

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871790B2