Reaktion #84283

ord-41bd32319c9141c3a2e89490c2af54d8

Reaktionsgleichung

COc1cnc(C(C)=O)c(Cl)c1
1-(3-chloro-5-methoxypyridin-2-yl)ethanone
C[N+](C)(C)c1ccccc1.C[N+](C)(C)c1ccccc1.C[N+](C)(C)c1ccccc1.[Br-].[Br-].[Br-]
trimethylphenylammonium tribromide
COc1cnc(C(=O)CBr)c(Cl)c1
desired product
Ausbeute 76.8%
COc1cnc(C(=O)CBr)c(Cl)c1
2-bromo-1-(3-chloro-5-methoxypyridin-2-yl)ethanone
Ausbeute 76.8%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter completion of the reaction
  2. 2
    Filtrationthe precipitated solid was filtered off
  3. 3
    Sonstigethe solvent was evaporated under reduced pressure
  4. 4
    SonstigeThe resulting residue was purified by silica gel column chromatography

Vorschrift

To 0.90 g of 1-(3-chloro-5-methoxypyridin-2-yl)ethanone in 10 ml of tetrahydrofuran, 1.82 g of trimethylphenylammonium tribromide was added, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the precipitated solid was filtered off, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent to obtain 0.57 g of the desired product as pale yellow crystals.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09434684B2uspto-grants-2016_09