p-Chlorothiophenol → 2-Nitro-4'-chloro diphenyl sulfide

HRID 2185930Notes

Reaction equation

HRID 2185930 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 3653942-Nitro-4'-chloro diphenyl sulfideYield 76.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2-Fluoronitrobenzene (1.5 g) and 4-chlorothio phenol (1.5 g) were dissolved in ethanol (30 ml) and potassium carbonate (1.4 g) was added thereto, followed by stirring at 60° C. for five hours. Subsequently, the solvent was removed under reduced pressure and the residue was dissolved in water (50 ml). The resultant solution was subjected to extraction with ethyl acetate (30 ml×2). The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was re-crystallized from diethyl ether, to thereby produce the target compound (2.1 g) as pale-brown crystals.

Workup

  1. customSubsequently, the solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in water (50 ml)
  3. extractionThe resultant solution was subjected to extraction with ethyl acetate (30 ml×2)
  4. washThe organic layer was washed sequentially with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was re-crystallized from diethyl ether

Sources & evidence

ORD record
ord-27df373a2b08438a9fcba83d897ff799
Source dataset
uspto-grants-2002_06
Patent number
US06403607B1

Reaction notes

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