Sodium Iodide → 2-Acetyl-4-(4-fluorophenyl)-4-oxobutyric acid ethyl ester

HRID 642217Notes

Reaction equation

HRID 642217 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4].[Na].[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16].[I-].[Na+]>CC(C)=O>[CH2:20]([O:19][C:13](=[O:18])[CH:14]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4])[C:15](=[O:16])[CH3:17])[CH3:21]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 1202482-Chloro-4'-fluoroacetophenoneHCID 87089461Ethyl acetoacetatesodium salt

Product 1

HCID 141739732-Acetyl-4-(4-fluorophenyl)-4-oxobutyric acid ethyl esterYield 98.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-chloro-1-(4-fluoro-phenyl)-ethanone (4.83 g, 28.0 mmol), ethyl acetoacetate sodium salt (4.26 g, 28.0 mmol) and sodium iodide (420 mg, 2.80 mmol) in acetone (50 mL) was refluxed for 1 h; then the solvents were evaporated, the residue was partitioned between EtOAc and 1 M HCl aqueous solution, the organic phase was washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, filtered, concentrated, to give a brown liquid, the title product (7.334 g); 1H NMR (200 MHz, CDCl3): δ (ppm)=8.1-7.9 (m, 2H), 7.2-7.1 (m, 2H), 4.22 (q, 2H, J=6.8 Hz), 4.2-4.0 (m, 1H), 3.8-3.4 (m, 2H), 2.44 (s, 3H), 1.30 (t, 3H, J=6.8 Hz).

Workup

  1. temperaturewas refluxed for 1 h
  2. customthen the solvents were evaporated
  3. customthe residue was partitioned between EtOAc and 1 M HCl aqueous solution
  4. washthe organic phase was washed with saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a brown liquid

Sources & evidence

ORD record
ord-0e667d3ea24e49ab86675a2981478649
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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