Potassium Iodide → Ethyl 2-(4-iodo-3-methoxyphenyl)propanoate

HRID 1428751Notes

Reaction equation

HRID 1428751 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[O:15][CH3:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.N([O-])=O.[Na+].[I-:33].[K+]>C(#N)C.O.C(OCC)(=O)C>[I:33][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[O:15][CH3:16]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 521998p-Toluenesulfonic acid monohydrateHCID 23668193Sodium NitriteHCID 86679376Ethyl 2-(4-amino-3-methoxyphenyl)propanoate

Product 1

HCID 70855859Ethyl 2-(4-iodo-3-methoxyphenyl)propanoateYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 2-(4-amino-3-methoxyphenyl)propanoate (447 mg, 2.002 mmol) in acetonitrile and water were added p-toluenesulfonic acid monohydrate (1.142 g, 6.006 mmol), sodium nitrite (276 mg, 4.004 mmol) and potassium iodide (831 mg, 5.005 mmol). The reaction mixture was stirred for 4 h at room temperature. The mixture dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. Ethyl 2-(4-iodo-3-methoxyphenyl)propanoate (468 mg) was obtained as 70% yield.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-8521c6db5caf4fbdad5ffe9c5d937b91
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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