2',4'-Dichloropropiophenone → 2-Bromo-1-(2,4-dichlorophenyl)propan-1-one

HRID 1418026Notes

Reaction equation

HRID 1418026 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:55][C:56]1[CH:61]=[C:60]([Cl:62])[CH:59]=[CH:58][C:57]=1[C:63](=[O:66])[CH2:64][CH3:65]>C(Cl)Cl.CO>[Br:1][CH:64]([CH3:65])[C:63]([C:57]1[CH:58]=[CH:59][C:60]([Cl:62])=[CH:61][C:56]=1[Cl:55])=[O:66]

Participants

5

Reactant 2

HCID 1234672',4'-DichloropropiophenoneHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 109239912-Bromo-1-(2,4-dichlorophenyl)propan-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

17.4 g of tetra-butylammonium tribromide are added at room temperature to 7 g of 1-(2,4-dichlorophenyl)propan-1-one in solution in a mixture of 420 ml of methylene chloride and 140 ml of methanol. After 24 hours, the reaction mixture is concentrated under vacuum. The residue is taken up in water and extracted with ethyl acetate, the organic phase is dried with sodium sulphate and evaporated under vacuum and the residue is then purified on a column of silica gel with a 20/1 (v/v) mixture of cyclohexane and ethyl acetate as eluent, to obtain an oil.

Workup

  1. concentrationthe reaction mixture is concentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase is dried with sodium sulphate
  4. customevaporated under vacuum
  5. customthe residue is then purified on a column of silica gel with a 20/1 (v/v) mixture of cyclohexane and ethyl acetate as eluent
  6. customto obtain an oil

Sources & evidence

ORD record
ord-c5fdd471b1e54633a7e2dfbb769a3f5f
Source dataset
uspto-grants-1999_03
Patent number
US05880135

Reaction notes

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