Reaction #6164

Reaction equation

sodium hydride

p-cyanophenol

1-bromo-5-chloro-pentane

hydrogen

→

4-(5-chloropentoxy) benzonitrile

Solvents

dimethylformamide

dimethylformamide

Conditions

Workup

1. 1
   TemperatureThe solution is then cooled in an ice-bath
2. 2
   workup.STIRRINGstirred for 18 h
3. 3
   workup.ADDITIONThe reaction is then poured onto water
4. 4
   Filtrationthe resulting solid filtered off
5. 5
   Otherdried

Procedure

To a solution of 16.9 g (135 mmol) p-cyanophenol in 169 mL of dimethylformamide (DMF), cooled in an ice-bath is added in portions 6.5 g (135 mmol) sodium hydride (50% dispersion in oil). The reaction is stirred and allowed to warm-up to room temperature until no further hydrogen evolution is observed. The solution is then cooled in an ice-bath and a solution of 1-bromo-5-chloro-pentane 25 g (135 mmol) in 84 mL of dimethylformamide is added. The reaction is allowed to warm up to room temperature and stirred for 18 h. The reaction is then poured onto water and the resulting solid filtered off and dried to give 4-(5-chloropentoxy) benzonitrile, m.p. 52°-54° C.

Source