Reacción #2876

ord-01265d1ee5214b12aaf7fb783abeb10c

Ecuación de reacción

O=C1CCC(=O)N1Br
N-bromosuccinimide
OCc1cc(Br)ccc1F
5-bromo-2-fluoro-benzyl alcohol
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenyl phosphine
Fc1ccc(Br)cc1CBr
title compound
Rendimiento 96.7%
Fc1ccc(Br)cc1CBr
5-Bromo-2-fluoro-benzyl bromide
Rendimiento 96.7%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe ice bath is removed
  2. 2
    OtroThe crude product is purified by column chromatography
  3. 3
    Lavadoeluting with 5% EtOAc/hexanes

Procedimiento

To a solution of 5-bromo-2-fluoro-benzyl alcohol (3.10 g, 15.1 mmol) in 30 mL of THF at 10° C. is added triphenyl phosphine (4.10 g, 15.6 mmol) followed by N-bromosuccinimide (2.67 g, 15.0 mmol). The ice bath is removed and the resulting solution is stirred for 20 min at room temperature. The crude product is purified by column chromatography eluting with 5% EtOAc/hexanes to give the title compound (3.90 g, 14.5 mmol).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05731315uspto-grants-1998_03