Acetonitrile → 3-(4-Fluoro-2-methylphenyl)-3-oxopropanenitrile

HRID 915563Notes

Reaction equation

HRID 915563 reaction equation
CCCCCC.[H-].[Na+].[F:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=O)=[C:12]([CH3:20])[CH:11]=1.[C:21](#[N:23])[CH3:22]>C(OCC)(=O)C.Cl.C1COCC1>[F:9][C:10]1[CH:19]=[CH:18][C:13]([C:14](=[O:16])[CH2:22][C:21]#[N:23])=[C:12]([CH3:20])[CH:11]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8058HexaneHCID 24758Sodium hydrideHCID 2782181Methyl 4-fluoro-2-methylbenzoate

Product 1

HCID 589586113-(4-Fluoro-2-methylphenyl)-3-oxopropanenitrileYield 99.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of hexane-washed sodium hydride (60% oil dispersion, 995 mg, 24.9 mmol) was added dropwise a THF solution (20 mL) of methyl 4-fluoro-2-methylbenzoate (3.8 g, 22.6 mmol) and anhydrous acetonitrile (2.4 mL, 45.2 mmol). The mixture was stirred at 70° C. for 16 h, and then cooled to rt. The resulting mixture was diluted with ethyl acetate (20 mL) and 1 N HCl (10 mL) and the layers were partitioned. The organic phase was washed with water (3×20 mL) and brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure to afford 4.0 g of yellow oil, which was taken to the next step without further purification. ES-MS m/z 178.2 (MH+); HPLC RT (min) 2.22.

Workup

  1. temperaturecooled to rt
  2. customthe layers were partitioned
  3. washThe organic phase was washed with water (3×20 mL) and brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1af060807fbe48a9b215e11704db396b
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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