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

HRID 468947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 468947
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ae9196610c2a4020b01dae47ea8c0a56
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623889B2

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