Reaction #47078

Reaction equation

chloroacetonitrile

3-fluorophenol

potassium carbonate

→

product 386

Yield 94.2%

3-Fluorophenoxyacetonitrile

Yield 94.2%

Solvents

EtOAc

DMF

Conditions

Workup

1. 1
   TemperatureThe reaction mixture is cooled to RT
2. 2
   Washwashed with water, brine
3. 3
   Dryingdried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   OtherThe filtrate is evaporated
6. 6
   Otherthe residue purified by chromatography on silica gel
7. 7
   Washelution with dichloromethane

Procedure

To a solution of 3-fluorophenol (560 mg, 5.0 mmol) in DMF (10 mL) is added potassium carbonate (828 mg, 6.0 mmol) followed by chloroacetonitrile (0.315 mL, 50.0 mmol). The reaction mixture is stirred and heated at 50° C. for 14 h. The reaction mixture is cooled to RT, diluted with EtOAc, and washed with water, brine, then dried (MgSO4), and filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with dichloromethane gives 712 mg of the product 386.

Source