Ethanol → HCID 68984517, compound

HRID 1257185Notes

Reaction equation

HRID 1257185 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 Et2O. The combined organic extracts were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by silica gel 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, 1H), 4.06 (m, 2H), 3.77 (s, 2H), 1.13 (t, J=6.9 Hz, 3H).

Workup

  1. extractionthe resultant solution was extracted with Et2O
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-664bd9a101814b5db03f5bace2c32a9e
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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