Sodium Cyanide → 2-(6-Bromopyridin-3-yl)acetonitrile

HRID 2375311Notes

Reaction equation

HRID 2375311 reaction equation
[C-:1]#[N:2].[Na+].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]Br)=[CH:7][N:6]=1>O1CCOCC1.O>[Br:4][C:5]1[N:6]=[CH:7][C:8]([CH2:11][C:1]#[N:2])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 64246602-Bromo-5-bromomethylpyridine

Product 1

HCID 177499762-(6-Bromopyridin-3-yl)acetonitrileYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of NaCN (117 g, 2.38 mol) in dioxane (1 L) and water (1 L), was added the above crude 2-bromo-5-bromomethylpyridine (275 g) and the mixture was stirred at rt for 15 h. The reaction mixture was quenched with cold water (15 L) and extracted with EtOAc (3×1 L). The organic layer was washed with water (3×1 L), brine (2×1 L), dried with Na2SO4 and concentrated under reduced pressure to give crude title compound. The crude residue was purified by column chromatography over silica gel (pet. ether/ethylacetate, 7:3) to give 95 g (6-bromopyridin-3-yl)acetonitrile as a pale yellow solid (49%). [TLC, Rf=0.5, pet. ether/ethylacetate 7:3]

Workup

  1. customThe reaction mixture was quenched with cold water (15 L)
  2. extractionextracted with EtOAc (3×1 L)
  3. washThe organic layer was washed with water (3×1 L), brine (2×1 L)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give crude title compound
  7. customThe crude residue was purified by column chromatography over silica gel (pet. ether/ethylacetate, 7:3)

Sources & evidence

ORD record
ord-2c21aadca3884bd18b6cb7191d2727ce
Source dataset
uspto-grants-2008_12
Patent number
US07465736B2

Reaction notes

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