반응 #1693

반응 방정식

2-cyano-5-(hydroxymethyl)thiophene

triphenylphosphine

carbon tetrabromide

→

2-cyano-5-(bromomethyl)thiophene

수율 75.0%

용매

THF

반응 조건

후처리

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

실험 절차

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.

출처