Dimethylformamide → Methyl 4-iodo-2-isopropoxybenzoate

HRID 531024Notes

Reaction equation

HRID 531024 reaction equation
I[CH:2]([CH3:4])[CH3:3].[OH:5][C:6]1[CH:15]=[C:14]([I:16])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[I:16][C:14]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([O:5][CH:2]([CH3:4])[CH3:3])[CH:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 11380407Methyl 4-iodosalicylate

Product 1

HCID 90422834Methyl 4-iodo-2-isopropoxybenzoateYield 98.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Iodopropane (6.42 g) was added at room temperature to a mixture of methyl 2-hydroxy-4-iodobenzoate (7.00 g), potassium carbonate (6.96 g), and DMF (100 mL), and the resultant mixture was stirred at 70° C. for 2 days 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 (7.92 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-52f1ca22a7b543f181ab4e59adb0ac88
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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