Dimethylformamide → 2-(2-Fluoro-3-methoxyphenyl)-2-methylpropanenitrile

HRID 1443146Notes

Reaction equation

HRID 1443146 reaction equation
[F:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][C:5]#N.[CH3:13]I.[H-].[Na+].C[N:18]([CH3:21])C=O>>[F:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([CH3:13])([CH3:5])[C:21]#[N:18]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 230744722-(2-Fluoro-3-methoxyphenyl)acetonitrile

Product 1

HCID 179892042-(2-Fluoro-3-methoxyphenyl)-2-methylpropanenitrileYield 99.5%

Procedure

4 g (24.22 mmol) of 2-fluoro-3-methoxybenzyl cyanide is dissolved in 38 ml of N,N-dimethylformamide and mixed with 6.87 g (48.35 mmol) of methyl iodide. At 0° C., 2.11 g (48.35 mmol) of sodium hydride (55%) is added in portions within 45 minutes. After 20 hours of stirring at room temperature, the batch is poured into ice water and extracted three times with 200 ml each of diethyl ether. The organic phases are washed with water and brine and dried. After the desiccant is filtered off and after the solvent is spun off, the residue is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane). 4.66 g (99.5%) of the desired compound is isolated.

Workup

  1. extractionextracted three times with 200 ml each of diethyl ether
  2. washThe organic phases are washed with water and brine
  3. customdried
  4. filtrationAfter the desiccant is filtered off
  5. customthe residue is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2181ed535dfb46c395556afaab119f32
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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