Potassium Cyanide → 2-(4-Chloro-3-fluorophenyl)acetonitrile

HRID 532781Notes

Reaction equation

HRID 532781 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([F:13])[CH:7]=1>CS(C)=O.O>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:1]#[N:2])=[CH:7][C:8]=1[F:13]

Participants

5

Reactant 2

HCID 9032Potassium Cyanide2×HCID 27831364-(Bromomethyl)-1-chloro-2-fluorobenzene

Product 1

HCID 38044142-(4-Chloro-3-fluorophenyl)acetonitrileYield 61.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

KCN (1.25 g, 19.2 mmol) was added to a solution of 4-(bromomethyl)-1-chloro-2-fluorobenzene (3.90 g, 17.5 mmol) in DMSO (60 mL). Several milliliters of H2O were added to help dissolve the KCN. After 1 hour, the reaction mixture was diluted with H2O and extracted with EtOAc. The extracts were dried (Na2SO4), filtered, and concentrated. The crude product was flashed on silica (Biotage 40M, 9:1 to 4:1 hex:EtOAc) to give 2-(4-chloro-3-fluorophenyl)acetonitrile (1.81 g, 61.2% yield) as a yellow crystalline solid.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d5531e5b49e646718f382b4858cdee01
Source dataset
uspto-grants-2014_10
Patent number
US08853199B2

Reaction notes

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