Water → HCID 13102715, compound

HRID 2290404Notes

Reaction equation

HRID 2290404 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+].C1(S([C:25]2[CH:30]=[CH:29][C:28]([S:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)(=[O:33])=[O:32])=[CH:27][N:26]=2)(=O)=O)C=CC=CC=1.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][C:25]1[CH:30]=[CH:29][C:28]([S:31]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)(=[O:33])=[O:32])=[CH:27][N:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72583,4-DichlorophenolHCID 13102684HCID 13102684, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13102715HCID 13102715, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4.08 g of 3,4-dichlorophenol dissolved in a 25 ml THF/25 DMSO mixture was added 2.9 g of t-BuOK and then 8.99 g of 2.5-bis(phenylsulfonyl)pyridine, and the resulting mixture heated at 58° C. for 11/2 hrs. The reaction mixture was cooled to room temperature, then added to 3 to 4 volumes of water and stirred. The brown precipitate which formed was removed by filtration. Recrystallization from CH2Cl2 /ethanol gave the purified product, 2-(3,4-dichlorophenoxy)-5-(phenylsulfonyl)pyridine (68% yield), as white shiny needles, m.p. 113°-114° C.

Workup

  1. customThe brown precipitate which formed
  2. customwas removed by filtration
  3. customRecrystallization from CH2Cl2 /ethanol

Sources & evidence

ORD record
ord-d81ac0933ec045b5a160168cf110535e
Source dataset
uspto-grants-1986_10
Patent number
US04616087

Reaction notes

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