Benzenesulfinic acid, sodium salt → 4-Benzenesulphonyl-2,6-dibromopyridine

HRID 1603548Notes

Reaction equation

HRID 1603548 reaction equation
[N+]([C:4]1[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([Br:11])[CH:5]=1)([O-])=O.[Na+].[C:13]1([S:19]([O-:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[C:13]1([S:19]([C:4]2[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([Br:11])[CH:5]=2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium saltHCID 160387482,6-Dibromo-4-nitropyridine

Product 1

HCID 541123304-Benzenesulphonyl-2,6-dibromopyridineYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

0.50 g (0.00177 mol) of 4-nitro-2,6-dibromopyridine and 0.29 g (0.00177 mol) of benzenesulphinic acid sodium salt were dissolved in 17 ml of dimethylformamide and stirred at 50° C. for 1 hr. 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 1:4 and subsequently dried in a high vacuum. There was obtained 0.59 g (88.5%) of 4-benzenesulphonyl-2,6-dibromopyridine as white crystals; m.p.: 134-135° 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 1:4
  7. customsubsequently dried in a high vacuum

Sources & evidence

ORD record
ord-0c03d7cee61149e4900c7375ecad5c4a
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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