Ethanol → 2-(3-Bromopyridin-2-yl)acetonitrile

HRID 2380866Notes

Reaction equation

HRID 2380866 reaction equation
[Br:1][C:2]1[C:3]([CH2:8]Br)=[N:4][CH:5]=[CH:6][CH:7]=1.C(O)C.O.[C-:14]#[N:15].[Na+]>ClCCl>[Br:1][C:2]1[C:3]([CH2:8][C:14]#[N:15])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 8929Sodium CyanideHCID 214410813-Bromo-2-(bromomethyl)pyridine

Product 1

HCID 6428252-(3-Bromopyridin-2-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above pyridine (5.13 g, 20.4 mmol) was stirred in 50.1 mL of a 5.6:1 solution of ethanol:deionized water. To this mixture was added sodium cyanide (1.20 g, 24.5 mmol), which was stirred for 2 hours and 30 minutes. The reaction mixture was diluted with dichloromethane (100 mL), washed with water (3×100 mL), and partitioned between water and dichloromethane. The organic layer was dried over sodium sulfate, filtered, concentrated, and subjected to silica gel chromatography eluting with 5-30% EtOAc in hexanes to yield (3-bromopyridin-2-yl)acetonitrile.

Workup

  1. washwashed with water (3×100 mL)
  2. custompartitioned between water and dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluting with 5-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-e1e4f723605347cca13b21b131e894e3
Source dataset
uspto-grants-2012_09
Patent number
US08258135B2

Reaction notes

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