Reaktion #2876

ord-01265d1ee5214b12aaf7fb783abeb10c

Reaktionsgleichung

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
Ausbeute 96.7%
Fc1ccc(Br)cc1CBr
5-Bromo-2-fluoro-benzyl bromide
Ausbeute 96.7%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05731315uspto-grants-1998_03