Reaction #6165

Reaction equation

4-(5-chloropentoxy) benzonitrile

sodium iodide

→

4-(5-iodopentoxy) benzonitrile

Solvents

acetone

acetone

Conditions

Workup

1. 1
   TemperatureThe reaction is heated
2. 2
   Temperatureto reflux
3. 3
   OtherThe acetone is removed under reduced pressure
4. 4
   Otherthe residue partitioned between water and ether
5. 5
   OtherThe ethereal layer is dried
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated

Procedure

To a solution of 32.7 g (146 mmol) of 4-(5-chloropentoxy) benzonitrile in 350 mL acetone is added 38.3 g (150 mmol) of sodium iodide in 230 mL of acetone. The reaction is heated to reflux and stirred overnight. The acetone is removed under reduced pressure and the residue partitioned between water and ether. The ethereal layer is dried, filtered and evaporated to give 4-(5-iodopentoxy) benzonitrile, m.p. 51°-54° C.

Source