Sodium Carbonate → 1-(2-Fluoro-phenylsulfanyl)-4-methyl-2-nitro-benzene

HRID 2358641Notes

Reaction equation

HRID 2358641 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](OS(C(F)(F)F)(=O)=O)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[SH:26].C([O-])([O-])=O.[Na+].[Na+]>CCO>[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5202162-FluorothiophenolHCID 713468894-Methyl-2-nitrophenyl trifluoromethanesulfonate

Product 1

HCID 684579081-(2-Fluoro-phenylsulfanyl)-4-methyl-2-nitro-benzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 4a (1.50 g, 5.3 mmol) and 2-fluorobenzenethiol (0.56 mL, 5.3 mmol) in EtOH (15 mL) was added aqueous Na2CO3 solution (0.563 g, 5.3 mmol) dropwise at room temperature. The mixture was heated to reflux fluxed for 1 hour, and then evaporated. The residue was diluted with EtOAc, washed with H2O, 5% KOH and brine, dried over MgSO4, filtered and concentrated under vacuum giving the title compound as yellow crystal, which was purified by washing with cold n-hexane to give the title product as yellow crystal (1.15 g, 83%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customevaporated
  4. additionThe residue was diluted with EtOAc
  5. washwashed with H2O, 5% KOH and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ca63dc1600c84b7f909db5487a12adb0
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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