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

HRID 709621Notes

Reaction equation

HRID 709621 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:17])C=1>C(#N)C>[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 98.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-bromo-2-methylpyridine (5.00 g) in acetonitrile (30 mL) was added 70% m-chloroperbenzoic acid (10.8 g), and the mixture was stirred at room temperature for 30 min. The resulting white precipitate was filtered off, and the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) and recrystallized (ethyl acetate/hexane) to give the title compound (5.36 g) as a pale-yellow solid.

Workup

  1. filtrationThe resulting white precipitate was filtered off
  2. customthe solvent in the filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)
  4. customrecrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c5bb8c4f60814553a4d9ec71561743b9
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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