Sodium Cyanide → 2-(6-Bromopyridin-2-yl)acetonitrile

HRID 2264375Notes

Reaction equation

HRID 2264375 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8]Br)[CH:5]=[CH:4][CH:3]=1.[C-:10]#[N:11].[Na+]>O1CCOCC1.O>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][C:10]#[N:11])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 129547962-Bromo-6-(bromomethyl)pyridine

Product 1

HCID 6428642-(6-Bromopyridin-2-yl)acetonitrileYield 40.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of the above crude 6-bromo-2-bromomethylpyridine (70 g, 0.28 mol) in dioxane (500 mL) and water (250 mL), was added NaCN (28 g, 0.74 mol) at 0° C. and then stirred at RT for 16 h. The reaction mixture was quenched with 3 Lit of water and extracted with ethylacetate (4×500 mL). The organic layer was washed with water (400 L), brine (250 mL), dried over Na2SO4 and concentrated to give crude product. The crude was purified by column chromatography over silica gel (pet. ether/ethylacetate, 8:2) to give 6-bromopyridine-2-yl-acetonitrile (22.5 g, 40%). [TLC: Pet. ether/ethylacetate, 7:3, Rf=0.35]

Workup

  1. customThe reaction mixture was quenched with 3 Lit of water
  2. extractionextracted with ethylacetate (4×500 mL)
  3. washThe organic layer was washed with water (400 L), brine (250 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude product
  7. customThe crude was purified by column chromatography over silica gel (pet. ether/ethylacetate, 8:2)

Sources & evidence

ORD record
ord-f7899f1205f7410e8b75a093342fbfed
Source dataset
uspto-grants-2010_12
Patent number
US07855212B2

Reaction notes

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