Acetic Acid → 3-Oxo-3-[2-(trifluoromethyl)phenyl]propanenitrile

HRID 1667652Notes

Reaction equation

HRID 1667652 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([F:17])([F:16])[F:15])=[O:7].ClCCl.C(O)(=O)C>O.C(O)C>[O:7]=[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([F:17])([F:16])[F:15])[CH2:5][C:1]#[N:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 27784302-Bromo-1-[2-(trifluoromethyl)phenyl]ethan-1-one

Product 1

HCID 126308073-Oxo-3-[2-(trifluoromethyl)phenyl]propanenitrileYield 70.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 26.04 g (0.40 mole) of potassium cyanide in 30 mL of water was added to a stirring solution of 27.00 g (0.10 mole) of 2-bromo-1-(2-trifluoromethyl-phenyl)-ethanone in 500 mL of ethanol. The mixture was stirred at room temperature overnight. Water and dichloromethane were added to the mixture. The mixture was then acidified with acetic acid (pH=5-6). The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Recrystallization of the residue with ether and hexane gave 14.97 g of 3-oxo-3(2-trifluoromethyl-phenyl)-propionitrile.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customRecrystallization of the residue with ether and hexane

Sources & evidence

ORD record
ord-f51da3a45fb04342aa0516bf04b3374c
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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