Dimethylformamide → 2-(3,4-Difluorophenyl)-2-methylpropanenitrile

HRID 1868778Notes

Reaction equation

HRID 1868778 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#N)[CH:5]=[CH:6][C:7]=1[F:8].CI.[CH3:14]C(C)([O-])C.[Na+].C[N:21]([CH:23]=O)C>CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:10])([CH3:14])[C:23]#[N:21])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 69572(3,4-Difluorophenyl)acetonitrileHCID 23676156Sodium t-butoxide

Product 1

HCID 552646522-(3,4-Difluorophenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-(3,4-Difluorophenyl)acetonitrile (25.0 g, 163 mmol) and MeI (25.4 mL, 408 mmol) were dissolved in DMF (163 mL) and added dropwise to a suspension of sodium tert-butoxide (39.2 g, 408 mmol) in DMF at 0° C. The resulting reaction mixture was stirred at 0° C. for 1 hour and then allowed to warm to ambient temperature for 1 hour. The reaction mixture was diluted with 400 mL of EtOAc, added to a separatory funnel, partitioned with water, washed 3 times with 200 mL of water, separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (26.45 g) as a yellow oil.

Workup

  1. customThe resulting reaction mixture
  2. temperatureto warm to ambient temperature for 1 hour
  3. additionadded to a separatory funnel
  4. custompartitioned with water
  5. washwashed 3 times with 200 mL of water
  6. customseparated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e07e9dbdd944d8e82c3027e2202ac5d
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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