Potassium Cyanide → 2-(5-Bromopyridin-3-yl)acetonitrile

HRID 2036810Notes

Reaction equation

HRID 2036810 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8]Cl)[CH:7]=1.[C-:10]#[N:11].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:10]#[N:11])[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 117012593-Bromo-5-(chloromethyl)pyridine

Product 1

HCID 150054172-(5-Bromopyridin-3-yl)acetonitrileYield 46.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromo-5-chloromethyl-pyridine (0.45 g; 2.2 mmol) was dissolved in DMF (10 mL). Potassium cyanide (0.21 g, 3.27 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was quenched by the addition of water and extracted with ethyl acetate. The organic phases were washed with water, brine and dried over Na2SO3 filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 7% EtOAc in Hexanes to provide 2-(5-bromopyridin-3-yl)acetonitrile (200 mg, 46.5%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.68 (d, 1H, J=2 Hz), 8.51 (d, 1H, J=2 Hz), 7.88 (t, 1H, J=2 Hz), 3.77 (s, 2H).

Workup

  1. customThe reaction mixture was quenched by the addition of water
  2. extractionextracted with ethyl acetate
  3. washThe organic phases were washed with water, brine
  4. dry with materialdried over Na2SO3
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-df3ae012fe9443bb874a9ae20185a312
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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