Tetra-n-butylammonium tribromide → HCID 57535421, compound

HRID 1455643Notes

Reaction equation

HRID 1455643 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.[Br-:15].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>[Br:15][C:10]1[C:9](=[O:14])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 68957992HCID 68957992, compound

Product 1

HCID 57535421HCID 57535421, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution 1-(4-chlorophenyl)pyridin-2(1H)-one (1 eq) and tetrabutylammonium tribromide (1.2 eq) in chloroform (0.1M) was stirred 6 h at reflux. The reaction mixture was diluted with aqueous NaHCO3 solution and aqueous Na2S2O3 solution. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (Hexane:EtOAc, 80:20) to afforded the title compound.

Workup

  1. temperatureat reflux
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (Hexane:EtOAc, 80:20)

Sources & evidence

ORD record
ord-62c99d886af749e598e0188767955943
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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