Potassium Iodide → HCID 86679385, compound

HRID 1428803Notes

Reaction equation

HRID 1428803 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[CH3:15].CC1C=CC(S(O)(=O)=O)=CC=1.O.N([O-])=O.[Na+].[I-:32].[K+].[OH-].[Na+]>C(#N)C.O.C(OCC)(=O)C>[I:32][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[CH3:15]

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 23668193Sodium NitriteHCID 58861806HCID 58861806, compound

Product 1

HCID 86679385HCID 86679385, compoundYield 84.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 2-(4-amino-3-methylphenyl)propanoate (944 mg, 4.55 mmol) in acetonitrile, p-TsOH.H2O (2.62 g, 13.66 mmol) was dropped slowly. The reaction mixture was activated for 10 min. Then NaNO2 (629 mg, 9.11 mmol) in water was added dropwise. The mixture was stirred for 10 min. Then potassium iodide (1.89 g, 11.39 mmol) in water was added slowly dropwise. The reaction mixture was stirred at room temperature for 4 h. After the reaction is complete, 1M NaOH solution was added to neutralize the reaction then ethyl acetate and water was used for work up. The organic layer was washed with water two times, then dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. Ethyl 2-(4-iodo-3-methylphenyl)propanoate (1.22 g) was obtained as 84% yield.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 h
  2. customthe reaction
  3. washThe organic layer was washed with water two times
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate removed in vacuo
  7. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-44a1e3ffbc0a45da89abe50699e54ff4
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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