Methyl iodide → 2-(2-Iodophenyl)propanenitrile

HRID 2078109Notes

Reaction equation

HRID 2078109 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[CH3:11]C(C)([O-])C.[Na+].CI>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:11])[C:9]#[N:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 44022822-IodophenylacetonitrileHCID 23676156Sodium t-butoxide

Product 1

HCID 668551472-(2-Iodophenyl)propanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2-Iodophenyl)acetonitrile (3.0 g, 12 mmol) and sodium tert-butoxide (3.6 g, 37 mmol) were stirred in 20 mL of DMF, and MeI (0.77 mL, 12 mmol) was added dropwise. The reaction was then stirred for 3 hours. The solvent was removed under vacuum. The crude residue was purified by silica flash chromatography 0-15% EtOAc/hexanes.

Workup

  1. customThe solvent was removed under vacuum
  2. customThe crude residue was purified by silica flash chromatography 0-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-17edfcb0b19d4741bf6fb33acd7f2e9b
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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