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

HRID 2427528Notes

Reaction equation

HRID 2427528 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.ClC1C=C(C(OO)=[O:17])C=CC=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N+:6]([O-:17])[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-olateYield 104.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 5-Bromo-2-methyl-pyridine (1.00 g, 5.80 mmol) in chloroform (10 mL) was slowly added 3-Chloro-benzenecarboperoxoic acid (1.004 g, 6.98 mmol) at 0° C. Stirring continued for 2 hrs at room temperature and the mixture was diluted with chloroform, washed with saturated sodium bicarbonate and water, dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound (1.14 g, 100%) as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 8.46 (s, 1H), 7.36 (d, 1H), 7.17 (d, 1H), 2.49 (s, 3H).

Workup

  1. customat 0° C
  2. washwashed with saturated sodium bicarbonate and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-42c13907ab6543ad8dc4f55657143dd2
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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