Reacción #710470

ord-af5cc388665046fb9f199acf3b3699c6

Ecuación de reacción

Cc1ccc(Br)nc1
2-bromo-5-methylpyridine
O=C1CCC(=O)N1Br
N-bromosuccinimide
BrCc1ccc(Br)nc1
2-bromo-5-bromomethylpyridine
Rendimiento 20.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturathe resulting mixture was heated
  2. 2
    Temperaturarefluxed for 19 hours
  3. 3
    Otrowas returned to room temperature
  4. 4
    Concentraciónconcentrated under reduced pressure
  5. 5
    Otropurified by silica gel column chromatography (hexane:ethyl acetate=19:1)

Procedimiento

500 mg (2.92 mmol) of 2-bromo-5-methylpyridine was dissolved in 15 ml of carbon tetrachloride, 623 mg (3.50 mmol) of N-bromosuccinimide and 10 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 19 hours. After the reaction was completed, the reaction solution was returned to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to obtain 143 mg (yield 20%) of 2-bromo-5-bromomethylpyridine.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09301525B2uspto-grants-2016_04