Iodine chloride → 2-(3-Ethoxy-4-iodo-phenyl)-2-methyl-propionitrile

HRID 2425582Notes

Reaction equation

HRID 2425582 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]([CH3:14])([CH3:13])[C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1)[CH3:2].[I:15]Cl>C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]([CH3:13])([CH3:14])[C:11]#[N:12])[CH:7]=[CH:8][C:9]=1[I:15])[CH3:2]

Participants

4

Reactant 2

HCID 24640Iodine chloride2×HCID 67245760HCID 67245760, compound

Product 1

HCID 672450572-(3-Ethoxy-4-iodo-phenyl)-2-methyl-propionitrileYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

2-(3-Ethoxy-phenyl)-2-methyl-propionitrile (2.96 grams, 15.65 mmol) was dissolved in a freshly prepared acetic acid solution of iodine monochloride (20 mL of a 1.54 M iodine monochloride solution in acetic acid, 30.8 mmol). The reaction was slightly exothermic. The reaction mixture was allowed to stand at room temperature for 3 d. The reaction mixture was concentrated, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with 10% sodium carbonate (1×), brine (1×), and dried (anhydrous magnesium sulfate). The solids were filtered off, and the filtrate was concentrated to dryness. The residue was purified by flash chromatography 110 g of silica gel, eluting with a gradient of ethyl acetate in hexanes) to give 2-(3-ethoxy-4-iodo-phenyl)-2-methyl-propionitrile (2.53 g, 51%). LR-MS: 316.21 [(M+H)+]

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with 10% sodium carbonate (1×), brine (1×)
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. filtrationThe solids were filtered off
  6. concentrationthe filtrate was concentrated to dryness
  7. customThe residue was purified by flash chromatography 110 g of silica gel
  8. washeluting with a gradient of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5c2bc20194ac4e1ca41972299338318a
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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