Reaction #2876

Reaction equation

N-bromosuccinimide

5-bromo-2-fluoro-benzyl alcohol

triphenyl phosphine

→

title compound

Yield 96.7%

5-Bromo-2-fluoro-benzyl bromide

Yield 96.7%

Solvents

THF

Conditions

Workup

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

Procedure

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).

Source