3,4-Dichlorophenol → 2-(3,4-Dichlorophenoxy)-5-(ethylsulfonyl)pyridine

HRID 1758005Notes

Reaction equation

HRID 1758005 reaction equation
CC([O-])(C)C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[CH:12][C:13]=1[Cl:14].C(S([C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH2:30][CH3:31])(=[O:29])=[O:28])=[CH:23][N:22]=1)(=O)=O)C>C1COCC1.CS(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[Cl:14])[O:15][C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH2:30][CH3:31])(=[O:28])=[O:29])=[CH:23][N:22]=1

Participants

6

Reactant 3

HCID 72583,4-DichlorophenolHCID 132780152,5-Bis(ethylsulfonyl)pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 131027052-(3,4-Dichlorophenoxy)-5-(ethylsulfonyl)pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 6.7 g of t-BuOK in a mixture of 50 ml of THF and 50 ml of DMSO was added 8.2 g of 3,4-dichlorophenol and then 7.9 g of 2,5-bis(ethylsulfonyl)pyridine, and the resulting mixture heated at 55° C. for 3 hrs. The reaction mixture was cooled and then poured into ice-water. A precipitate formed which was collected by filtration and then washed with water. The recovered solid was then dissolved in CH2Cl2 and dried over MgSO4. The solution was diluted with an equal volume of hexane and treated with silica gel and then filtered. The solution was then concentrated to 50 ml, cooled and 6.5 g of 2-(3,4-dichlorophenoxy)-5-ethylsulfonyl)pyridine recovered as a white powder, m.p. 117°-118° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customA precipitate formed which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. dissolutionThe recovered solid was then dissolved in CH2Cl2
  6. dry with materialdried over MgSO4
  7. additionThe solution was diluted with an equal volume of hexane
  8. additiontreated with silica gel
  9. filtrationfiltered
  10. concentrationThe solution was then concentrated to 50 ml
  11. temperaturecooled
  12. custom6.5 g of 2-(3,4-dichlorophenoxy)-5-ethylsulfonyl)pyridine recovered as a white powder, m.p. 117°-118° C.

Sources & evidence

ORD record
ord-6d43749f31324507b7834d7845047778
Source dataset
uspto-grants-1983_02
Patent number
US04371537

Reaction notes

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