p-Fluoronitrobenzene → HCID 19605525, compound

HRID 1603607Notes

Reaction equation

HRID 1603607 reaction equation
[K].[CH3:2][C:3]1[CH:4]=[C:5]([SH:10])[CH:6]=[C:7]([CH3:9])[CH:8]=1.F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>CN1CCCC1=O>[CH3:9][C:7]1[CH:6]=[C:5]([S:10][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:4]=[C:3]([CH3:2])[CH:8]=1

Participants

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 70001724HCID 70001724, compound

Product 1

HCID 19605525HCID 19605525, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

0.25 g (0.0014 mol) of 3,5-dimethylthiophenol potassium salt were dissolved in 5 ml of 1-methyl-2-pyrrolidone, treated with 0.19 g (0.00134 mol) of 1-fluoro-4-nitrobenzene and a spatula tip of Cu powder and stirred at 160° C. for about 5 hrs. Thereafter, the solvent was removed by distillation, the residue was partitioned in water/ethyl acetate and the organic phase was washed with sat. sodium chloride solution and dried over MgSO4. After filtration and removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane 1:15. There was obtained 0.22 g (62%) of 1,3-dimethyl-5-(4-nitrophenylsulphanyl)-benzene as a viscous, yellow oil. MS (EI): me/e=259 (C14H13NO2S+).

Workup

  1. customThereafter, the solvent was removed by distillation
  2. customthe residue was partitioned in water/ethyl acetate
  3. washthe organic phase was washed with sat. sodium chloride solution
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration and removal of the solvent the residue
  6. customwas chromatographed on silica gel with ethyl acetate/hexane 1:15

Sources & evidence

ORD record
ord-a9dd3f209e0d460e9344df15682080b4
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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