Reacción #1350609

ord-fb1d8e3ff39145dca07086394b8e5f07

Ecuación de reacción

N#[C][Cu]
Copper(I) cyanide
Cc1ccc(Br)cc1F
4-bromo-2-fluorotoluene
Cc1ccc(C#N)cc1F
title compound
Rendimiento 58.0%
Cc1ccc(C#N)cc1F
2-fluoro-4-cyanotoluene
Rendimiento 58.0%

Disolventes

Condiciones de reacción

Temperatura
150°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaAfter cooling to room temperature
  2. 2
    Otrothe mixture was partitioned between water and EtOAc (500 mL each)
  3. 3
    SecadoThe organic layer was dried (MgSO4), and solvent
  4. 4
    Otrowas removed under vacuum

Procedimiento

Copper(I) cyanide (Aldrich, 3.6 g, 40 mmol) was added to a solution of 4-bromo-2-fluorotoluene (Aldrich, 5 g, 27 mmol) in DMF (60 mL). The reaction mixture was heated at 150° C. for 11 hours. After cooling to room temperature, the mixture was partitioned between water and EtOAc (500 mL each). The organic layer was dried (MgSO4), and solvent was removed under vacuum to give the title compound (2.08, 58%). 1HNMR (CDCl3) δ2.36 (s, 3H), 7.30 (m, 3H), 7.35 (d, 1H, J=8.1 Hz).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06541467B1uspto-grants-2003_04