Dimethylformamide → Ethyl 7-(2,4,6-triiodophenoxy)heptanoate

HRID 914643Notes

Reaction equation

HRID 914643 reaction equation
CN(C)C=O.Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[I:18][C:19]1[CH:24]=[C:23]([I:25])[CH:22]=[C:21]([I:26])[C:20]=1[OH:27].C(=O)([O-])[O-].[K+].[K+]>O>[I:18][C:19]1[CH:24]=[C:23]([I:25])[CH:22]=[C:21]([I:26])[C:20]=1[O:27][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 122490Ethyl 7-bromoheptanoate

Product 1

HCID 22939821Ethyl 7-(2,4,6-triiodophenoxy)heptanoateYield 187.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylformamide (DMF, 20 mL) was added with ethyl 7-bromoheptanoate (4.7 g) and 2,4,6-triiodophenol (2.4 g), further added with potassium carbonate (2.1 g) and stirred at room temperature for one day. The reaction solution was added with water and extracted twice with ethyl acetate, and the organic layer was washed three times with water and dried over anhydrous magnesium sulfate. Then, the solvent was removed, and the resulting residue was purified by silica gel column chromatography to obtain ethyl 7-(2,4,6-triiodophenoxy)heptanoate (6.0 g, yield: 96%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washthe organic layer was washed three times with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThen, the solvent was removed
  5. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2a19ebada4d547a3994400506714300a
Source dataset
uspto-grants-2007_09
Patent number
US07264790B2

Reaction notes

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