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

HRID 1945589Notes

Reaction equation

HRID 1945589 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:17])C=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N+:3]=1[O-:17]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 131787372-Bromo-5-methylpyridine 1-oxideYield 91.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-bromo-5-methylpyridine (2.0 g, 11.6 mmol) and 3-chloroperbenzoic acid (3.0 g, 14.8 mmol) in chloroform (7 mL) was stirred at 50° C. for 3 hours, cooled down to room temperature and filtered. The filtrate was concentrated under reduced pressure to give a residue that was purified by flash chromatography (Si—PPC, MeOH:EtOAc, gradient 0:100 to 10:90) to give 2-Bromo-5-methylpyridine 1-oxide as a white solid (2.0 g, 91%). 1H NMR (400 MHz, CHCl3-d): δ 8.24 (s, 1 H); 7.52 (d, J=8.3 Hz, 1 H); 6.93 (d, J=8.33 Hz, 1 H); 2.29 (s, 3 H).

Workup

  1. temperaturecooled down to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give a residue that
  5. customwas purified by flash chromatography (Si—PPC, MeOH:EtOAc, gradient 0:100 to 10:90)

Sources & evidence

ORD record
ord-d2edd791902844359b0a36349c17f1cf
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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