Potassium Cyanide → 2-(4-Chloro-2,6-difluorophenyl)acetonitrile

HRID 1806953Notes

Reaction equation

HRID 1806953 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH2:6]Br)=[C:4]([F:11])[CH:3]=1.[C-:12]#[N:13].[K+]>C(O)C.O>[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH2:6][C:12]#[N:13])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 27735514-Chloro-2,6-difluorobenzyl bromide

Product 1

HCID 27735722-(4-Chloro-2,6-difluorophenyl)acetonitrileYield 58.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Step A To the solution of 4-chloro-2,6-difluorobenzyl bromide (Alfa) (2.5 g, 10 mmol) in ethanol (13 mL) and H2O (10 mL) was added KCN (1.75 g, 27 mmol). The reaction mixture was heated at 100° C. for 1 h. The mixture was cooled, and extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous NaHCO3 solution, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:4) to give (4-chloro-2,6-difluoro-phenyl)-acetonitrile as a yellow oil (1.1 g, 57%).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous NaHCO3 solution, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (EtOAc:hexanes=1:4)

Sources & evidence

ORD record
ord-3598869d53b24274aa7588b42cf789f2
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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