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

HRID 399620Notes

Reaction equation

HRID 399620 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)-1-propanone dissolved in a mixture of 420 ml of methylene chloride and 140 ml of methanol. After 24 hours, the reaction medium is evaporated to dryness under vacuum. The residue is taken up in water and extracted with ethyl acetate, and the organic phase is dried over sodium sulphate. The solvent is evaporated off under vacuum and the product is then purified on a column of silica, using a mixture of cyclohexane and ethyl acetate (20:1 v/v) as eluent.

Workup

  1. customthe reaction medium is evaporated to dryness under vacuum
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. customThe solvent is evaporated off under vacuum
  5. customthe product is then purified on a column of silica
  6. additiona mixture of cyclohexane and ethyl acetate (20:1 v/v) as eluent

Sources & evidence

ORD record
ord-4d065df3619947c6adf48ccb147483f4
Source dataset
uspto-grants-1998_10
Patent number
US05821255

Reaction notes

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