Water → ethyl 2-(4-fluoroanilino)acetate

HRID 2368466Notes

Reaction equation

HRID 2368466 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.C([O-])(=O)C.[Na+].O>C(O)C>[F:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 97314-FluoroanilineHCID 517045Sodium Acetate

Product 1

HCID 711751ethyl 2-(4-fluoroanilino)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl bromoacetate (8.09 g, 48.4 mmol) was slowly added to a solution of 4-fluoroaniline (5.38 g, 48.4 mmol) and sodium acetate (5.16 g, 62.9 mmol) in ethanol (62 mL) and the mixture was heated at 80° C. for 2 h. Water was added and the reaction was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-20% EtOAc in hexanes) to afford ethyl 2-((4-fluorophenyl)amino)acetate (1).

Workup

  1. extractionthe reaction was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f457b6a7fd064308b17e398bd1692f47
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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