HCID 569606, compound → 4-(Bromoacetyl)phenyl benzoate

HRID 910638Notes

Reaction equation

HRID 910638 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-:19].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>CO>[C:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16](=[O:18])[CH2:17][Br:19])=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 569606HCID 569606, compoundHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 2203054-(Bromoacetyl)phenyl benzoateYield 73.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

13.50 g (corresponding to 59.66 mmol) of 4′-benzoyloxyacetophenone was dissolved in 1100 ml of methanol, and 34.52 g (corresponding to 71.59 mmol) of tetra-n-butylammonium tribromide was added thereto. The mixture was stirred overnight at room temperature, and was distilled off under reduced pressure to remove the solvent. The residue was dissolved in ethyl acetate and washed twice with water and then washed with an aqueous saturated sodium chloride solution. After the ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, the resulting crude product was purified by silica gel column chromatography (elution solvent: hexane/methylene chloride=1/1), to obtain 13.38 g (corresponding to 43.84 mmol) of 4′-benzoyloxy-2-bromoacetophenone (FIG. 5, Step 4).

Workup

  1. distillationwas distilled off under reduced pressure
  2. customto remove the solvent
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed twice with water
  5. washwashed with an aqueous saturated sodium chloride solution
  6. dry with materialAfter the ethyl acetate layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting crude product was purified by silica gel column chromatography (elution solvent: hexane/methylene chloride=1/1)

Sources & evidence

ORD record
ord-7bbaba2568f04649824921737ff6ed9a
Source dataset
uspto-grants-2011_09
Patent number
US08022207B2

Reaction notes

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