Water → 3-(3-Chlorophenoxy)nitrobenzene

HRID 1797030Notes

Reaction equation

HRID 1797030 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.F[C:16]1[CH:17]=[C:18]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:20][CH:21]=1.O>CS(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][C:16]1[CH:17]=[C:18]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79333-ChlorophenolHCID 98231-Fluoro-3-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 221751693-(3-Chlorophenoxy)nitrobenzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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.

Workup

  1. temperatureThe resulting dark mixture was heated at 120° C. for 12 hours
  2. temperaturecooled to room temperature
  3. extractionThe resulting mixture was extracted with ether (2×200 mL)
  4. washThe organic fraction was washed with 2N NaOH (100 mL)
  5. dry with materialAfter drying (MgSO4)
  6. customthe solvent was evaporated
  7. distillationthe resulting dark oil was distilled

Sources & evidence

ORD record
ord-bc71cf3db8d847f5991aa342c8d00d60
Source dataset
uspto-grants-2006_04
Patent number
US07034035B2

Reaction notes

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