Hydrogen Peroxide → 2-Bromo-6-methylpyridine 1-oxide

HRID 631833

Reaction equation

HRID 631833 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[OH:9]O>C(O)(=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N+:3]=1[O-:9]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 792052-Bromo-6-methylpyridine

Product 1

HCID 36520842-Bromo-6-methylpyridine 1-oxideYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2-Bromo-6-methylpyridine (36 g, 0.2 mol) was dissolved in acetic acid (700 ml), hydrogen peroxide (30%, 62 ml, 0.6 mol) was added and the mixture was stirred at 90° C. for 24 hours. After cooling to room temperature, the mixture was diluted with water (700 ml) and extracted with DCM (4×). The combined organic phases were washed with water, dried (sodium sulfate) and concentrated under reduced pressure to give 36 g of a red-brown liquid (0.19 mol, 94%) MS(APCI) m/z=188.0 [M+1]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with DCM (4×)
  3. washThe combined organic phases were washed with water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0174e97f34374a7eb9ad52ca8502bfa9
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Linked notes

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