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

HRID 1435869Notes

Reaction equation

HRID 1435869 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]Br)=[N:6][CH:7]=1.[C-:10]#[N:11].[K+]>CCO.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:10]#[N:11])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 234380625-Bromo-2-(bromomethyl)pyridine

Product 1

HCID 29927881(5-Bromopyridin-2-yl)acetonitrileYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 5-bromo-2-(bromomethyl)pyridine (0.70 g, 2.12 mmole), in EtOH (50 mL) at 60° C. was added KCN (0.21 g, 3.18 mmole) in H2O (3 mL). After 1.5 h, the reaction contents were cooled to RT and concentrated under vacuum. The aqueous residue was dissolved in EtOAc and washed with H20, and dried over Na2SO4. Concentration under vacuum and purification on silica (EtOAc) afforded the title compound (0.38 g, 65%) as light yellow solid: LC-MS (ES) m/e 277 (M+H)+.

Workup

  1. customthe reaction contents
  2. concentrationconcentrated under vacuum
  3. dissolutionThe aqueous residue was dissolved in EtOAc
  4. washwashed with H20
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration
  7. customunder vacuum and purification on silica (EtOAc)

Sources & evidence

ORD record
ord-af30409053374449a540fb07cc33599f
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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