Ethanol → HCID 68984517, compound

HRID 1930412Notes

Reaction equation

HRID 1930412 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=[O:14].[CH3:16][CH2:17]O>OS(O)(=O)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 702EthanolHCID 68986061HCID 68986061, compound

Product 1

HCID 68984517HCID 68984517, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of (2,4-difluoro-5-nitro-phenyl)acetic acid (16 g, 74 mmol) in EtOH (200 mL) and 98% H2SO4 (14 mL) was refluxed at 80° C. for 2.5 h under a N2 atmosphere. The reaction mixture was poured into ice-water, and the resultant solution was extracted with ether. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography to give ethyl 2-(2,4-difluoro-5-nitrophenyl)acetate (16 g, 89% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.22 (t, J=8.1 Hz, 1H), 7.55 (t, J=11.1 Hz, 1 H), 4.06 (m, 2 H), 3.77 (s, 2 H), 1.13 (t, J=6.9 Hz, 3 H).

Workup

  1. extractionthe resultant solution was extracted with ether
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-832d1048e035459881286bb31fc18854
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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