3,4-Dichlorophenol → Pyridine, 2-(3,4-dichlorophenoxy)-3-(methylsulfonyl)-

HRID 1758012Notes

Reaction equation

HRID 1758012 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[CH:12][C:13]=1[Cl:14].CS([C:20]1[C:25]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=1)(=O)=O>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[Cl:14])[O:15][C:20]1[C:25]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 13102687HCID 13102687, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 514894Pyridine, 2-(3,4-dichlorophenoxy)-3-(methylsulfonyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Potassium t-butoxide (2.47 g) was dissolved in 30 ml of THF and then 3.46 g of 3,4-dichlorophenol dissolved in THF was added. A solution of 5.00 g of 2,3-bis(methylsulfonyl)pyridine in 20 ml THF/20 ml DMSO was added dropwise. The resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was poured onto ice-water which resulted in the formation of an oil which solidified on standing. The product was collected by filtration and dried in a vacuum oven and 5.33 g of material obtained. Recrystallization from CH2Cl2 /hexane gave purified 2-(3,4-dichlorophenoxy)-3-(methylsulfonyl)pyridine, m.p. 95°-96° C.

Workup

  1. additionwas added
  2. additionThe reaction mixture was poured onto ice-water which
  3. customresulted in the formation of an oil which
  4. filtrationThe product was collected by filtration
  5. dry with materialdried in a vacuum oven and 5.33 g of material
  6. customobtained
  7. customRecrystallization from CH2Cl2 /hexane
  8. customgave
  9. custompurified 2-(3,4-dichlorophenoxy)-3-(methylsulfonyl)pyridine, m.p. 95°-96° C.

Sources & evidence

ORD record
ord-396e3d148598417f8b5219a4fb8ca005
Source dataset
uspto-grants-1983_02
Patent number
US04371537

Reaction notes

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