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

HRID 1175621Notes

Reaction equation

HRID 1175621 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][N:3]=1.[C-:10]#[N:11].[Na+]>CCO>[Br:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][C:10]#[N:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 64246602-Bromo-5-bromomethylpyridine

Product 1

HCID 177499762-(6-Bromopyridin-3-yl)acetonitrileYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-5-(bromomethyl)pyridine (example 40e) (6 g, 24 mmol) and NaCN (1.42 g, 29 mmol) in absolute EtOH (50 mL) was heated at 80° C. for 8 h. The mixture was then cooled to room temperature then evaporated. The residue was suspended in water and extracted with EtOAc. The organic phase was washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel (5-30% EtOAc/hexanes) to give 2.89 g (63%) of 2-(6-Bromopyridin-3-yl)acetonitrile. 1H NMR (400 MHz, dMSO): δ 4.07 (s, 2H), 7.66-7.68 (d, 1H), 7.72-7.73 (dd, 1H), 8.36-8.37 (d, 1H).

Workup

  1. customthen evaporated
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel (5-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1e6462edef2940cbab71ba63a4260208
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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