Water → HCID 13102692, compound

HRID 1757998Notes

Reaction equation

HRID 1757998 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].CS([C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][N:20]=1)(=O)=O.O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][N:20]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 131026752,5-Bis(methylsulfonyl)pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 13102692HCID 13102692, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 18.4 g of 4-bromophenol dissolved in a 80 ml THF/80 ml DMSO mixture was added 13.1 g of t-BuOK and then 25.0 g of 2,5-bis(methylsulfonyl)pyridine, and the resulting mixture heated at 58° C. for 11/2 hrs. The reaction mixture was cooled overnight and then poured into 3 volumes of water and stirred. The pink-white crystalline product was filtered, dissolved in CH2Cl2 and dried over MgSO4. Recrystallization from ethanol gave purified 2-(4-bromophenoxy)-5-(methylsulfonyl)pyridine, (55% yield), as white shiny needles, m.p. 125°-126° C.

Workup

  1. temperatureThe reaction mixture was cooled overnight
  2. filtrationThe pink-white crystalline product was filtered
  3. dissolutiondissolved in CH2Cl2
  4. dry with materialdried over MgSO4
  5. customRecrystallization from ethanol
  6. customgave

Sources & evidence

ORD record
ord-328fd5b1ca1d4e54a7f20c9113a063af
Source dataset
uspto-grants-1983_02
Patent number
US04371537

Reaction notes

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