Dimethylformamide → Methyl 2-ethoxy-4-iodobenzoate

HRID 531038Notes

Reaction equation

HRID 531038 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-iodobenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Iodoethane (6.47 mL) was added to a mixture of methyl 2-hydroxy-4-iodobenzoate (15 g), potassium carbonate (14.9 g), and DMF (100 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 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 (16.5 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with saturated saline
  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-db17a1da3744405ca66873a9eee24286
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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