4-Fluoro-3-methylphenylacetonitrile → 2-(4-Fluoro-3-methylphenyl)acetamide

HRID 546774Notes

Reaction equation

HRID 546774 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[CH3:11].C[Si](C)(C)[O:14][K].O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:10])=[O:14])=[CH:4][C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 201118384-Fluoro-3-methylphenylacetonitrileHCID 86585896Sodium bicarbonate waterHCID 178504318HCID 178504318, compound

Product 1

HCID 668394032-(4-Fluoro-3-methylphenyl)acetamideYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

4-Fluoro-3-methylphenylacetonitrile (1.1 g) was dissolved in toluene (35 ml), and trimethylsiloxypotassium (3.7 g) was added. After stirring at 110° C. for 2.5 hours, saturated sodium bicarbonate water was added, followed by separation with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to obtain 863 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customfollowed by separation with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11ced35569554d9dae2da493e6af642b
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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