Iodide Ion → HCID 21867266, compound

HRID 857150Notes

Reaction equation

HRID 857150 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[C:7]([Br:21])[CH:6]=1.[I-:23]>S([O-])([O-])(=O)=O.[Ag+].[Ag+].CO>[Br:11][C:9]1[CH:10]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:22])[CH:6]=[C:7]([Br:21])[C:8]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([I:23])[CH:14]=1

Participants

5

Reactant 2

HCID 30165Iodide IonHCID 15495991HCID 15495991, compound

Product 1

HCID 21867266HCID 21867266, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 159865Silver sulfateCatalystHCID 887MethanolSolvent

Procedure

Methyl[3,5-dibromo-4-(4-methoxyphenoxy)phenyl]acetate (1.0 g, 2.3 mmol), silver (I) sulfate (1.6 g, 4.6 mmol) and methanol (10 mL) was stirred in the dark at −78° C. Iodide (1.2 g, 4.6 mmol) was added and the reaction mixture was allowed to reach room temperature after 10 minutes. The yellow precipitate was filtered off, the eluate dissolved in ethyl actetate and washed with water. After concentration of the organic phase, 0.82 g (64%) of methyl [3,5-dibromo-4-(4-methoxy-3-iodophenoxy)phenyl]acetate was obtained.

Workup

  1. filtrationThe yellow precipitate was filtered off
  2. dissolutionthe eluate dissolved in ethyl actetate
  3. washwashed with water

Sources & evidence

ORD record
ord-fa91f8a2bdeb42ebabc5c9cf521d4fff
Source dataset
uspto-grants-2006_12
Patent number
US07144909B2

Reaction notes

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