Reaction #2845

Reaction equation

4-hydroxymethyl-thiophene-2-carbonitrile

triphenyl phosphine

carbon tetrabromide

→

title compound

Yield 95.8%

4-Bromomethyl-thiophene-2-carbonitrile

Yield 95.8%

Solvents

THF

Conditions

Workup

1. 1
   Filtrationthe solution is filtered
2. 2
   Concentrationconcentrated
3. 3
   OtherThe crude product is purified by column chromatography
4. 4
   Washeluting with gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes

Procedure

To a solution of 4-hydroxymethyl-thiophene-2-carbonitrile (10 g, 72 mmol), in 360 mL of THF is added triphenyl phosphine (18.3 g, 76 mmol) and carbon tetrabromide (25 g, 76 mmol). After 3 h, the solution is filtered and concentrated. The crude product is purified by column chromatography eluting with gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes to afford the title compound (14 g, 69 mmol) as a white solid.

Source