Ethyl Acetate → Ethyl (3-iodobenzoyl)acetate

HRID 1375683Notes

Reaction equation

HRID 1375683 reaction equation
C(O[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([I:11])[CH:6]=1)C.CC([O-])(C)C.[K+].[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20]>C1COCC1.Cl>[I:11][C:7]1[CH:6]=[C:5]([C:4](=[O:12])[CH2:20][C:19]([O:22][CH2:23][CH3:24])=[O:21])[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 143542Ethyl 3-iodobenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 2759369Ethyl (3-iodobenzoyl)acetateYield 100.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl-3-iodobenzoate (25.4 g, 92.0 mmol) was dissolved in THF (60 mL) and cooled to 0° C. followed by the addition of KOt-Bu (20.6 g, 184 mmol). The mixture was stirred for 15 minutes followed by the addition of ethyl acetate (8.91 g, 101 mmol). The mixture was warmed to ambient temperature, stirred for 2 hours, diluted with aqueous HCl (10%, 200 mL) and extracted with ethyl acetate (2×150 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to provide the titled compound (29.3 g, 100%).

Workup

  1. temperatureThe mixture was warmed to ambient temperature
  2. stirringstirred for 2 hours
  3. extractionextracted with ethyl acetate (2×150 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80f7233abdc5461e8aa356d65a5e0ba6
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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