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

HRID 1423066Notes

Reaction equation

HRID 1423066 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+].CCOC(C)=O.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-bromopyridin-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, EtOAc (80 mL) and saturated aqueous sodium bicarbonate (40 mL) are added and the organic layer is 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% EtOAc in heptane to afford (2-bromopyridin-4-yl)-acetonitrile. MS m/z 197.4, 199.4.

Workup

  1. customthe organic layer is 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% EtOAc in heptane

Sources & evidence

ORD record
ord-3e0f8e4c476041038193bf14a8149326
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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