Reaktion #84254

ord-cd850f646e874edab909d8c8af2c313c

Reaktionsgleichung

CC(=O)c1ncc(Cl)cc1Cl
1-(3,5-dichloropyridin-2-yl)ethanone
C[N+](C)(C)c1ccccc1.C[N+](C)(C)c1ccccc1.C[N+](C)(C)c1ccccc1.[Br-].[Br-].[Br-]
trimethylphenylammonium tribromide
O=C(CBr)c1ncc(Cl)cc1Cl
desired product
Ausbeute 161.1%
O=C(CBr)c1ncc(Cl)cc1Cl
2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone
Ausbeute 161.1%

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 through celite
  3. 3
    Sonstigethe solvent was evaporated under reduced pressure
  4. 4
    SonstigeThe resulting residue was purified by silica gel column chromatography

Vorschrift

To 5.00 g of 1-(3,5-dichloropyridin-2-yl)ethanone in 75 ml of tetrahydrofuran, 9.94 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 through celite, 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 5:95 to 15:85) as the eluent to obtain 6.64 g of the desired product as a brown oil.

Quelle

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