Trifluoroacetic acid → 1-(4-Bromo-2-nitrophenyl)butane-1,3-dione

HRID 69110Notes

Reaction equation

HRID 69110 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([CH:8]([C:16](=[O:18])[CH3:17])C(OC(C)(C)C)=O)=[O:7])=[C:4]([N+:21]([O-:23])=[O:22])[CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:20]=[CH:19][C:5]([C:6](=[O:7])[CH2:8][C:16](=[O:18])[CH3:17])=[C:4]([N+:21]([O-:23])=[O:22])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86694315Tert-butyl 2-(4-bromo-2-nitrobenzoyl)-3-oxobutanoate

Product 1

HCID 866943141-(4-Bromo-2-nitrophenyl)butane-1,3-dioneYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 4.95 g of tert-butyl 2-(4-bromo-2-nitrobenzoyl)-3-oxobutanoate in 30 mL of dichloromethane was added 20 mL of trifluoroacetic acid under ice-cooling. The mixture was warmed to room temperature and stirred for 2.5 hours, and then the solvent was evaporated under reduced pressure. To the residue was added ethyl acetate, and the solution was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 2.7 g of 1-(4-bromo-2-nitrophenyl)butane-1,3-dione.

Workup

  1. temperaturecooling
  2. customthe solvent was evaporated under reduced pressure
  3. additionTo the residue was added ethyl acetate
  4. washthe solution was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8af8931798734c489dbb562b145b2b07
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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