تفاعل #2876

ord-01265d1ee5214b12aaf7fb783abeb10c

معادلة التفاعل

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

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05731315uspto-grants-1998_03