Water → 3-(3-Chlorophenoxy)nitrobenzene

HRID 584714Notes

Reaction equation

HRID 584714 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-17b9016fef444ece8d4615ef1cbea93b
Source dataset
uspto-grants-2005_08
Patent number
US06927225B2

Reaction notes

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