HCID 9957460, compound → HCID 10720846, compound

HRID 380453Notes

Reaction equation

HRID 380453 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:20])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6].I[C:22]1C=C(C=C(I)[C:30]=1OC1C=CC(OC)=CC=1)C(Cl)=O>>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:20])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:5]([O:7][CH2:22][CH3:30])=[O:6]

Participants

3

Reactant 2

HCID 9957460HCID 9957460, compoundHCID 18349331HCID 18349331, compound

Product 1

HCID 10720846HCID 10720846, compound

Conditions

Temperature
70 °C

Procedure

Ethyl 3,5-diiodo-4-(4′-methoxyphenoxy)benzoate (Compound 5) was synthesized by way of 3,5-diiodo-4-(4′-20 methoxyphenoxy) benzoyl chloride, the latter having been described in Borrows et al., supra. Thus, in a 10 ml flask 3,5-diiodo-4-(4′methoxyphenoxy)benzoic acid (99.2 mg, 0.200 mmole) was converted to 3,5-diiodo-4-(4′-methoxyphenoxy) benzoyl chloride. After removal of excess thionyl chloride under vacuum, anhydrous ethanol (5.0 ml) was added with stirring and the mixture heated to 70° C. for 5 minutes. Excess ethanol was removed and the dry residue dissolved in hot 95% ethanol (4.0 ml), from which the product ester crystallized in the refrigerator (3° C.). Yield: 55.8 mg (53%) of buff-colored crystals. Melting point: 96-98° C.

Workup

  1. customAfter removal of excess thionyl chloride under vacuum, anhydrous ethanol (5.0 ml)
  2. additionwas added
  3. customExcess ethanol was removed
  4. dissolutionthe dry residue dissolved in hot 95% ethanol (4.0 ml), from which the product ester
  5. customcrystallized in the refrigerator (3° C.)

Sources & evidence

ORD record
ord-3b23d35b56b54c72b1b1cd0f17a99ec5
Source dataset
uspto-grants-2001_10
Patent number
US06303621B1

Reaction notes

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