Trifluoroacetic acid → Ethyl 3-fluoro-4-nitro-5-benzyloxyphenylacetate

HRID 1372652Notes

Reaction equation

HRID 1372652 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:29]([O-:31])=[O:30])=[C:11]([F:28])[CH:12]=[C:13]([CH:15](C(OCC)=O)[C:16]([O:18][C:19](C)(C)[CH3:20])=[O:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10]([N+:29]([O-:31])=[O:30])=[C:11]([F:28])[CH:12]=[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67406365Tert-butyl ethyl 5-benzyloxy-3-fluoro-4-nitrophenylmalonate

Product 1

HCID 17859018Ethyl 3-fluoro-4-nitro-5-benzyloxyphenylacetateYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (30 ml) was dissolved tert-butyl ethyl 5-benzyloxy-3-fluoro-4-nitrophenylmalonate (2.89 g, 6.67 mmol) . To the resulting solution was added trifluoroacetic acid (30 ml). The resulting mixture was stirred at room temperature for 3.5 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. The residue was neutralized with an aqueous saturated solution of sodium bicarbonate, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from ethyl acetate/hexane (1/5) eluate fractions, ethyl 5-benzyloxy-3-fluoro-4-nitrophenylacetate (1.57 g, 70%) was obtained as a yellow oil.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column, whereby from ethyl acetate/hexane (1/5) eluate fractions

Sources & evidence

ORD record
ord-5621ce6c9c4d41bf8e586c41bbc2c57f
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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