Water → HCID 67439536, compound

HRID 1664823Notes

Reaction equation

HRID 1664823 reaction equation
[H-].[Na+].[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11][C:12]#[N:13].Br[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].O>CN(C)C=O>[C:12]([CH:11]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([F:10])[C:4]=1[F:3])[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 5189682,3-Difluorophenylacetonitrile

Product 1

HCID 67439536HCID 67439536, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 2.9 g, 71.8 mmol) was slowly added to a solution of (2,3-difluorophenyl)acetonitrile (10.0 g, 65.3 mmol) and ethyl 4-bromobutanoate (12.7 g, 65.3 mmol) in N,N-dimethylformamide (100 mL) at 0° C. After 30 min, the reaction mixture was warmed to ambient temperature. After 3 h, water was added and the mixture was extracted with ethyl acetate (2×). The organic extracts were washed with saturated aqueous ammonium chloride, saturated brine, dried over magnesium sulfate, filtered and concentrated to give the title compound. MS 267.1 (M+1).

Workup

  1. waitAfter 3 h
  2. extractionthe mixture was extracted with ethyl acetate (2×)
  3. washThe organic extracts were washed with saturated aqueous ammonium chloride, saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f67257c29b9842b8b49fdd45af105466
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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