Methanol → Methyl [4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetate

HRID 1506670

Reaction equation

HRID 1506670 reaction equation
[CH:1]1[C:2]([CH2:19][C:20]([OH:22])=[O:21])=[CH:3][C:4]([I:18])=[C:5]([O:8][C:9]2[CH:10]=[C:11]([I:17])[C:12]([OH:16])=[C:13]([I:15])[CH:14]=2)[C:6]=1[I:7].O=S(Cl)Cl.O.[CH3:28]O>>[CH3:28][O:21][C:20](=[O:22])[CH2:19][C:2]1[CH:1]=[C:6]([I:7])[C:5]([O:8][C:9]2[CH:10]=[C:11]([I:17])[C:12]([OH:16])=[C:13]([I:15])[CH:14]=2)=[C:4]([I:18])[CH:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24386Thionyl ChlorideHCID 65552Tetraiodothyroacetic acid

Product 1

HCID 52919069Methyl [4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetateYield 61%

Procedure

In anhydrous conditions, Tetrac (5.0 g, 6.7 mmol, 1.0 eq.) was dissolved in anhydrous methanol (200 mL). To the solution was then added dropwise SOCl2 (485 μL, 6.7 mmol, 1.0 eq.). The reaction was set to reflux for 2 days. Water was then added to the reaction medium (200 mL) and then the solution was concentrated to yield a precipitate. The precipitate was then collected by vacuum filtration and then recrystallized to give orange crystals (3.10 g, 4.0 mmol) of methyl-2-(4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)acetate in 61% yield.

Workup

  1. temperatureto reflux for 2 days
  2. concentrationthe solution was concentrated
  3. customto yield a precipitate
  4. filtrationThe precipitate was then collected by vacuum filtration
  5. customrecrystallized

Sources & evidence

ORD record
ord-9a873be399864dfaa1312637e351248f
Source dataset
uspto-grants-2015_12
Patent number
US09220788B2

Linked notes

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