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

HRID 61001Notes

Reaction equation

HRID 61001 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([O-])(O)=O.[Na+]>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

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 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 (10 g, 58.13 mmol) and meta-chloroperbenzoic acid (mCPBA, 30 g, 174.39 mmol) in CHCl3 (160 mL) was heated at 60° C. for 16 h. The mixture was cooled to rt and neutralized with satd. NaHCO3. The resulting mixture was extracted with DCM. The organic layers were combined and washed with brine and dried (MgSO4). The solvent was removed in vacuo. The crude was purified by silica gel chromatography (EtOAc/hexanes) to obtain the title compound.

Workup

  1. extractionThe resulting mixture was extracted with DCM
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed in vacuo
  5. customThe crude was purified by silica gel chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-dac80aaa1eac40c39c5b1e78352c0f96
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

Loading…