3-(Trifluoromethyl)benzenethiol → 2,6-Dibromo-4-(3-trifluoromethylphenylsulphanyl)-pyridine

HRID 1603598Notes

Reaction equation

HRID 1603598 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[Br:12][C:13]1[CH:18]=[C:17]([N+]([O-])=O)[CH:16]=[C:15]([Br:22])[N:14]=1>CN(C)C=O>[Br:12][C:13]1[CH:18]=[C:17]([S:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=2)[CH:16]=[C:15]([Br:22])[N:14]=1

Participants

4

Reactant 2

HCID 1367513-(Trifluoromethyl)benzenethiolHCID 160387482,6-Dibromo-4-nitropyridine

Product 1

HCID 196055152,6-Dibromo-4-(3-trifluoromethylphenylsulphanyl)-pyridineYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g (0.0056 mol) of 3-trifluoromethylthiophenol was dissolved in 17 ml of dimethylformamide and treated with 0.64 g (0.0056 mol) of potassium tert.-butylate. The mixture was stirred at room temperature for 20 min. and then treated with 1.58 g (0.0056 mol) of 2,6-dibromo-4-nitro-pyridine. The mixture was stirred at room temperature for 3 hrs., the solvent was then removed and the residue was partitioned in water and ethyl acetate. The organic phase was washed with sat. sodium chloride solution, dried over MgSO4, filtered and, after removal of the solvent, the residue was chromatographed on silica gel with ethyl acetate/hexane 1:39. There was obtained 2.08 g (90%) of 2,6-dibromo-4-(3-trifluoromethylphenylsulphanyl)-pyridine as yellow crystals; m.p.: 68-70° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hrs
  2. custom, the solvent was then removed
  3. customthe residue was partitioned in water
  4. washThe organic phase was washed with sat. sodium chloride solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customafter removal of the solvent
  8. customthe residue was chromatographed on silica gel with ethyl acetate/hexane 1:39

Sources & evidence

ORD record
ord-1b108b04855f483caadeafed5a948964
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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