Reaction #2336520

Reaction equation

water

3-fluoronitrobenzene

potassium t-butoxide

3-chlorophenol

→

3-(3-chlorophenoxy)nitrobenzene

Solvents

DMSO

Conditions

Workup

1. 1
   TemperatureThe resulting dark mixture was heated at 120° C. for 12 hours
2. 2
   Temperaturecooled to room temperature
3. 3
   ExtractionThe resulting mixture was extracted with ether (2×200 mL)
4. 4
   WashThe organic fraction was washed with 2N NaOH (100 mL)
5. 5
   DryingAfter drying (MgSO4)
6. 6
   Otherthe solvent was evaporated
7. 7
   workup.DISTILLATIONthe resulting dark oil was distilled

Procedure

To a stirred solution of potassium t-butoxide (12.3 g) in DMSO (100 mL) was added at once 3-chlorophenol (12.86 g). The resulting solution was stirred for 5 minutes at room temperature, then 3-fluoronitrobenzene (12.70 g) was added all at once. The resulting dark mixture was heated at 120° C. for 12 hours, cooled to room temperature then poured into water (700 mL). The resulting mixture was extracted with ether (2×200 mL). The organic fraction was washed with 2N NaOH (100 mL), then with water (100 mL). After drying (MgSO4), the solvent was evaporated and the resulting dark oil was distilled to give 3-(3-chlorophenoxy)nitrobenzene as a yellow oil, b.p. 135-140° C. at 0.05 mm

Source