HCID 9957460, compound → HCID 10720846, compound

HRID 1598345Notes

Reaction equation

HRID 1598345 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](Cl)=[O:6].IC1C=[C:24](C=C(I)C=1OC1C=CC(OC)=CC=1)[C:25](O)=[O:26]>>[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:26][CH2:25][CH3:24])=[O:6]

Participants

3

Reactant 2

HCID 9957460HCID 9957460, compoundHCID 18349331HCID 18349331, compound2×

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'-methoxyphenoxy)benzoyl chloride, the latter having been described in Borrows et al., 1949, J. Chem. Soc. 1949: S185-S190. 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-91108798636f4eb79adadebbd5e94dbc
Source dataset
uspto-grants-1998_04
Patent number
US05736576

Reaction notes

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