Trifluoroacetic acid → Methyl (3-bromo-4-nitrophenyl)acetate

HRID 494393Notes

Reaction equation

HRID 494393 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([Br:21])[CH:13]=1)C(OC(C)(C)C)=O.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([Br:21])[CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 576832692-(3-Bromo-4-nitrophenyl)malonic acid tert-butyl ester methyl ester

Product 1

HCID 23512304Methyl (3-bromo-4-nitrophenyl)acetateYield 94.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The 2-(3-bromo-4-nitrophenyl)malonic acid tert-butyl ester methyl ester (1.18 g) obtained in Example 4 a) was dissolved in chloroform (10 mL), trifluoroacetic acid (10 g) was added thereto under ice-cooling, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured gradually into ice and saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over sodium sulfate and concentrated to give the title compound (0.820 g) as a pale yellow oil.

Workup

  1. temperatureunder ice-cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-add141723c084d18b251c5a51095c2a1
Source dataset
uspto-grants-2009_05
Patent number
US07538140B2

Reaction notes

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