Acetic Acid → 4-Chlorobenzoylacetonitrile

HRID 1667656Notes

Reaction equation

HRID 1667656 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:7].C(O)(=O)C>C(O)C.O.ClCCl>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:6](=[O:7])[CH2:5][C:1]#[N:2])=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 68303p-Chlorophenacyl bromide

Product 1

HCID 1383084-Chlorobenzoylacetonitrile

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.58 g (86 mmole) of potassium cyanide and 1 mL of water was added in one portion to a solution of 8.0 g (34.3 mmole) of α-bromo-p-chloroacetophenone in 50 mL of 95% ethanol. The mixture was stirred at room temperature for 5 hours, then diluted with water and dichloromethane and acidified with acetic acid. The organic layer was washed with brine. The aqueous layers were extracted with dichloromethane. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give crude 3-(4-chloro-phenyl)-3-oxo-propionitrile which was used in next step without further purification.

Workup

  1. washThe organic layer was washed with brine
  2. extractionThe aqueous layers were extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02aed5e9865f4d5eb4d87c5682f5ca4c
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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