Water → Pyridine, 2-(3,4-dichlorophenoxy)-5-(methylsulfonyl)-

HRID 1758003Notes

Reaction equation

HRID 1758003 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].CC([O-])(C)C.[K+].CS([C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][N:21]=1)(=O)=O.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][N:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72583,4-DichlorophenolHCID 131026752,5-Bis(methylsulfonyl)pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 514892Pyridine, 2-(3,4-dichlorophenoxy)-5-(methylsulfonyl)-Yield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 3,4-dichlorophenol (13.8 g) dissolved in a 60 ml THF/60 ml DMSO mixture was added 9.5 g of t-BuOK. The temperature rose to about 40° C. and then 19.8 g of 2,5-bis(methylsulfonyl)pyridine was added. The reaction mixture was warmed to 50° C. and the temperature maintained at 50° C. for 1 hour. The reaction mixture was cooled, poured into approximately 3 volumes of water and the solid collected. The solid was dried on a porous plate and then recrystallized from CH2Cl2 /ethanol to give 23.5 g of 2-(3,4-dichlorophenoxy)-5-(methylsulfonyl)pyridine as shiny white plates, m.p. 120°-121° C.

Workup

  1. customrose to about 40° C.
  2. temperaturethe temperature maintained at 50° C. for 1 hour
  3. temperatureThe reaction mixture was cooled
  4. customthe solid collected
  5. customThe solid was dried on a porous plate
  6. customrecrystallized from CH2Cl2 /ethanol

Sources & evidence

ORD record
ord-c9f4a87b8c3749ff91d6b4d79c0e889d
Source dataset
uspto-grants-1983_02
Patent number
US04371537

Reaction notes

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