Dimethylformamide → Methyl 2-ethoxy-4-iodobenzoate

HRID 531050Notes

Reaction equation

HRID 531050 reaction equation
I[CH2:2][CH3:3].[OH:4][C:5]1[CH:14]=[C:13]([I:15])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:2]([O:4][C:5]1[CH:14]=[C:13]([I:15])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])[CH3:3]

Participants

6

Reactant 4

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

Product 1

HCID 66635397Methyl 2-ethoxy-4-iodobenzoateYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Iodoethane (3.53 g) was added at room temperature to a mixture of methyl 2-hydroxy-4-iodobenzoate (4.19 g), potassium carbonate (4.17 g), and DMF (50 mL), and the resultant mixture was stirred at 70° C. for 1 hour in a nitrogen atmosphere. Water was added to the reaction mixture at room temperature, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline in this order 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 (4.52 g).

Workup

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

Sources & evidence

ORD record
ord-bf8bd9de33e24aeba79e92ffad3a5066
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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