m-Chloroperbenzoic acid → 5-Bromo-2-methylpyridin-1-ium-1-olate

HRID 1466563Notes

Reaction equation

HRID 1466563 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:14]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N+:6]([O-:14])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12010205-Bromo-2-methylpyridine

Product 1

HCID 8171645-Bromo-2-methylpyridin-1-ium-1-olate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5-bromo-2-methylpyridine (2.0 g, 12 mmol, 1.0 eq) and m-chloroperoxybenzoic acid (70%, 2.89 g, 12.9 mmol, 1.1 eq) in 30 mL chloroform was stirred at room temperature for 4 hours. The reaction mixture was then partitioned between dichloromethane and 2 M aqueous sodium carbonate. The aqueous layer was extracted once more with dichloromethane, and the combined organic portions dried over magnesium sulfate and concentrated to give 5-bromo-2-methylpyridine 1-oxide. LCMS (ESI) m+H=189.0; 1H NMR (400 MHz, DMSO-d6) δ: 8.57 (s, 1H), 7.50 (d, 1H), 7.45 (d, 1H), 2.30 (s, 3H).

Workup

  1. customThe reaction mixture was then partitioned between dichloromethane and 2 M aqueous sodium carbonate
  2. extractionThe aqueous layer was extracted once more with dichloromethane
  3. dry with materialthe combined organic portions dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-83e501746e8f4c44b13b9e813d006583
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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