Water → HCID 13102706, compound

HRID 1758007Notes

Reaction equation

HRID 1758007 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+].CC(S([C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH:31]([CH3:33])[CH3:32])(=[O:30])=[O:29])=[CH:24][N:23]=1)(=O)=O)C.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH:31]([CH3:33])[CH3:32])(=[O:29])=[O:30])=[CH:24][N:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72583,4-DichlorophenolHCID 13102678HCID 13102678, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13102706HCID 13102706, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4.89 g of 3,4-dichlorophenol dissolved in a 25 ml THF/25 ml DMSO mixture was added 3.2 g of t-BuOK and then 8.74 g of 2,5-bis((1-methylethyl)sulfonyl)pyridine, and the resulting mixture was heated at 58° C. for 11/2 hrs. The reaction mixture was allowed to cool overnight and then poured in approximately 3 to 4 volumes of water and stirred. The yellow-white precipitate which formed was removed by filtration. Recrystallization from CH2Cl2 /ethanol gave the product, 2-(3,4-dichlorophenoxy)-5-((1-methylethyl)sulfonyl)pyridine, (42% yield), as tiny white needles, m.p. 91°-92° C.

Workup

  1. temperatureto cool overnight
  2. customThe yellow-white precipitate which formed
  3. customwas removed by filtration
  4. customRecrystallization from CH2Cl2 /ethanol

Sources & evidence

ORD record
ord-e2a91973983d479a803a497c596f7d35
Source dataset
uspto-grants-1983_02
Patent number
US04371537

Reaction notes

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