Water → HCID 13102709, compound

HRID 1758008Notes

Reaction equation

HRID 1758008 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+].C(S([C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])(=[O:32])=[O:31])=[CH:26][N:25]=1)(=O)=O)CCCCC.O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])(=[O:31])=[O:32])=[CH:26][N:25]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 13102680HCID 13102680, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13102709HCID 13102709, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4.33 g of 4-bromophenol dissolved in a 22 ml THF/22 ml DMSO mixture was added 3.1 g of t-BuOK and then 9.39 g of 2,5-bis(n-hexylsulfonyl)pyridine, and the resulting mixture heated at 59° C. for 1 hr. The reaction mixture was cooled to room temperature and then added to approximately 4 to 5 volumes of water. The yellow precipitate which formed was removed by filtration. Recrystallization from CH2Cl2 /ethanol gave the product, 2-(4-bromophenoxy)-5-(n-hexylsulfonyl)pyridine, (52% yield), as white shiny prisms, m.p. 94° C.

Workup

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

Sources & evidence

ORD record
ord-3b131e5fcd064bf687a08a3aab510fe0
Source dataset
uspto-grants-1983_02
Patent number
US04371537

Reaction notes

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