Hydrochloric Acid → p-Fluorobenzoylacetonitrile

HRID 133512Notes

Reaction equation

HRID 133512 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4].[C-:12]#[N:13].[K+].Cl>C(O)C.O>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][C:12]#[N:13])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 2783172p-FluorobenzoylacetonitrileYield 6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 2.5 g (11.5 mmol) 2-bromo-1-(4-fluoro-phenyl)-ethanone (the preparation of which is described in example . . . ) in 40 ml ethanol was added a solution of 0.90 g (23 mmol) potassium cyanide in 9 ml water. The mixture was then stirred at RT for 2 h, then acidified to ph=5-6 with aqueous HCl 1M and then extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 6:1) afforded 0.11 g (6%) 3-(4-fluoro-phenyl)-3-oxo-propionitrile as a yellow solid.

Workup

  1. customthe preparation of which
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d794914686c042e9bcf6f9e4d4485bfe
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

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