Ethyl Acetate → 2-(2-Bromopyridin-4-YL)acetonitrile

HRID 2172962Notes

Reaction equation

HRID 2172962 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]OS(C)(=O)=O)[CH:5]=[CH:4][N:3]=1.[C-:14]#[N:15].[K+].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:14]#[N:15])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 86672755HCID 86672755, compound

Product 1

HCID 534290262-(2-Bromopyridin-4-YL)acetonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Methanesulfonic acid 2-bromo-pyridin-4-ylmethyl ester (4.24 g, 15.9 mmol) is added to a stirred solution of potassium cyanide (1.02 g, 15.1 mmol) in a mixture of ethanol (30 mL) and water (6 mL) at room temperature. After 72 hours, ethyl acetate (80 mL) and saturated aqueous sodium bicarbonate (40 mL) are added and phases are separated. The organic layer is washed with water (3×40 mL), dried over MgSO4, filtered and concentrated. The resulting residue is purified by silica gel chromatography eluting with a gradient of 0-60% ethyl acetate in heptane to afford (2-bromo-pyridin-4-yl)-acetonitrile (ES+ m/z 197.41; 199.40).

Workup

  1. customphases are separated
  2. washThe organic layer is washed with water (3×40 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue is purified by silica gel chromatography
  7. washeluting with a gradient of 0-60% ethyl acetate in heptane

Sources & evidence

ORD record
ord-c417e6e0903f419786dfb7a16bc7de4c
Source dataset
uspto-grants-2015_06
Patent number
US09056858B2

Reaction notes

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