2,6-Dibromo-4-nitropyridine → 2,6-Dibromo-4-(4-nitrophenylsulphanyl)-pyridine

HRID 1603555Notes

Reaction equation

HRID 1603555 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([Br:11])[N:3]=1.[K].[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1)([O-:15])=[O:14]>CN(C)C=O>[Br:11][C:4]1[CH:5]=[C:6]([S:22][C:19]2[CH:20]=[CH:21][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=2)[CH:7]=[C:2]([Br:1])[N:3]=1

Participants

4

Reactant 2

HCID 160387482,6-Dibromo-4-nitropyridineHCID 700026814Nitrothiophenol potassium salt

Product 1

HCID 108836442,6-Dibromo-4-(4-nitrophenylsulphanyl)-pyridineYield 83.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.48 g (0.0025 mol) of 2,6-dibromo-4-nitropyridine and 0.70 g (0.0024 mol) of 4nitrothiophenol potassium salt were dissolved in 12.5 ml of dimethylformamide and stirred at room temperature for 3 hrs. The solvent was removed and the residue was partitioned in water and ethyl acetate. The combined organic phases were 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 1:19 and subsequently dried in a high vacuum. There was obtained 0.785 g (81%) of 2,6-dibromo-4-(4-nitrophenylsulphanyl)-pyridine as yellow crystals; m.p. 166-168° C.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned in water
  3. washThe combined organic phases were 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 1:19
  7. customsubsequently dried in a high vacuum

Sources & evidence

ORD record
ord-e7dbdcb833d24efca35dab68c158df14
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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