Iodine → 4-(2-Iodo-5-methoxyphenyl)butan-2-one

HRID 4281Notes

Reaction equation

HRID 4281 reaction equation
[I:1]I.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][C:13](=[O:15])[CH3:14])[CH:8]=[CH:9][CH:10]=1>C(O)(=O)C.C([O-])(=O)C.[Ag+]>[I:1][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][C:7]=1[CH2:11][CH2:12][C:13](=[O:15])[CH3:14]

Participants

5

Reactant 2

HCID 807IodineHCID 114239024-(3-Methoxyphenyl)butan-2-one

Product 1

HCID 140254744-(2-Iodo-5-methoxyphenyl)butan-2-oneYield 82.3%

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 176Acetic AcidSolvent

Procedure

Samples of iodine (42.4 g, 0.167 mole) and silver acetate (27.87 g, 0.167 mole) were added in portions to a solution of 29.8 g (0.167 mole) of 1-(3-methoxyphenyl)butane-3-one in 167 ml of glacial acetic acid. The mixture was stirred one hour. The silver iodide was removed by filtration and washed with acetic acid. The filtrate was partitioned between ether and water. The ether layer was washed with water, sodium bicarbonate solution and sodium thiosulfate solution. The ether solution was dried with MgSO4 and evaporated to dryness in vacuo. There was obtained 41.8 g (82% yield) of oily 1-(2-iodo-5-methoxyphenyl)butane-3-one.

Workup

  1. customThe silver iodide was removed by filtration
  2. washwashed with acetic acid
  3. customThe filtrate was partitioned between ether and water
  4. washThe ether layer was washed with water, sodium bicarbonate solution and sodium thiosulfate solution
  5. dry with materialThe ether solution was dried with MgSO4
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-986aa5b3e849477ab861a73561ebea06
Source dataset
uspto-grants-1988_02
Patent number
US04725602

Reaction notes

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