Dimethylformamide → Methyl 2-ethoxy-4-iodobenzoate

HRID 531117Notes

Reaction equation

HRID 531117 reaction equation
I[CH2:2][CH3:3].CN(C=O)C.[OH:9][C:10]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:2]([O:9][C:10]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 11380407Methyl 4-iodosalicylate

Product 1

HCID 66635397Methyl 2-ethoxy-4-iodobenzoateYield 98.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Iodoethane (2.75 g) was added to a DMF (40 mL) suspension of methyl 2-hydroxy-4-iodobenzoate (3.27 g) and potassium carbonate (3.25 g), and the mixture was stirred at 60° C. for 24 hours. The reaction mixture was allowed to cool to room temperature, and then, water was added thereto, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (3.53 g).

Workup

  1. temperatureto cool to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe obtained organic layer was washed with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-176634836f884ff095f469e9d0922661
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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