m-Chloroperbenzoic acid → HCID 67976751, compound

HRID 468906Notes

Reaction equation

HRID 468906 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([Cl:9])[C:5]([CH3:8])=[N:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:16]>ClCCl>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([Cl:9])[C:5]([CH3:8])=[N+:6]([O-:16])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67974202HCID 67974202, compound

Product 1

HCID 67976751HCID 67976751, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-bromo-3-chloro-2,4-dimethylpyridine (441 mg; 2.0001 mmol) in dichloromethane (10 mL; 156.0 mmol) was added 3-chloroperoxybenzoic acid (70%, 0.5547 g; 2.250 mmol). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with additional dichloromethane (100 mL), washed with saturated sodium bicarbonate, dried over magnesium sulfate, filtered, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (40 g silica, solvent gradient: 0-100% ethyl acetate in dichloromethane) to yield 374.1 mg (79%) of the title compound. LCMS (ESI): M+H=236.2; 1H NMR (400 MHz, DMSO) δ 8.65 (s, 1H), 2.47 (s, 3H), 2.43 (s, 3H).

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude product was purified via flash chromatography on silica gel (40 g silica, solvent gradient: 0-100% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-3eb0fce377704c3fa6a6903c2a1dded7
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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