Iodoethane → Ethyl 4-ethoxy-3-iodobenzoate

HRID 746769Notes

Reaction equation

HRID 746769 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([I:12])[CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH3:22].CCOC(C)=O>C(#N)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:21][CH3:22])=[C:7]([I:12])[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11220038Ethyl 4-hydroxy-3-iodobenzoate

Product 1

HCID 44829074Ethyl 4-ethoxy-3-iodobenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To the resultant ester (3.10 g, 10.61 mmol) and potassium carbonate (2.87 g, 20.75 mmol) in 40 ml acetonitrile, add iodoethane (1.3 ml, 16.25 mmol) at RT while stirring vigorously. Heat the resulting white suspension under reflux for 1.5 h. Evaporate acetonitrile and replace with EtOAc. Wash the organic layer first with water, then with saturated aq. sodium chloride. Dry over anhydrous sodium sulfate, filter and concentrate to give the title compound as a yellow oil.

Workup

  1. temperatureHeat the resulting white suspension
  2. temperatureunder reflux for 1.5 h
  3. washWash the organic layer first with water
  4. dry with materialDry over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-e0e2f0eb362345f4b8af51323376579c
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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