Reacción #1693

Ecuación de reacción

2-cyano-5-(hydroxymethyl)thiophene

triphenylphosphine

carbon tetrabromide

→

2-cyano-5-(bromomethyl)thiophene

Rendimiento 75.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in chloroform
3. 3
   LavadoThe product was eluted
4. 4
   workup.ADDITIONFractions containing pure product (as judged by TLC)
5. 5
   Concentraciónconcentrated in vacuo

Procedimiento

To a solution of 2-cyano-5-(hydroxymethyl)thiophene (6.0 g, 43 mmol) in THF (50 mL) was added triphenylphosphine (15.7 g, 47 mmol) and carbon tetrabromide (12.3 g, 47 mmol). After stirring overnight under nitrogen atmosphere at room temperature, the solvent was removed in vacuo and the residue was dissolved in chloroform, then adsorbed onto silica gel and loaded onto a silica gel column. The product was eluted using an ethyl acetate/hexanes gradient. Fractions containing pure product (as judged by TLC) were pooled and concentrated in vacuo to give 6.5 g (75%) of 2-cyano-5-(bromomethyl)thiophene.

Fuente