m-Chloroperbenzoic acid → 3-Bromo-5-fluoro-2,4-dimethylpyridine 1-oxide

HRID 468947Notes

Reaction equation

HRID 468947 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[CH3:8].ClC1C=C(C=CC=1)C(OO)=[O:16]>ClCCl>[Br:1][C:2]1[C:3]([CH3:10])=[N+:4]([O-:16])[CH:5]=[C:6]([F:9])[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 679747603-Bromo-5-fluoro-2,4-dimethylpyridine

Product 1

HCID 679750773-Bromo-5-fluoro-2,4-dimethylpyridine 1-oxideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-bromo-5-fluoro-2,4-dimethyl-pyridine (220 mg, 1.08 mmol) and 3-chloroperoxybenzoic acid (399 mg, 1.62 mmol) in dichloromethane (3 mL) was stirred overnight at room temperature. The reaction mixture was diluted with DCM (50 mL) and washed with saturated aqueous sodium thiosulfite (10 mL) followed by saturated aqueous sodium bicarbonate (10 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue that was purified by flash chromatography (4 g, Silica, 0-10% methanol in DCM). Desired fractions were combined and evaporated in vacuo to afford the title compound as a white solid (220 mg, 93%), which was used in the next step without further purification.

Workup

  1. washwashed with saturated aqueous sodium thiosulfite (10 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a residue that
  7. customwas purified by flash chromatography (4 g, Silica, 0-10% methanol in DCM)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-ae9196610c2a4020b01dae47ea8c0a56
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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