1-Bromooctane → HCID 20200552, compound

HRID 979492Notes

Reaction equation

HRID 979492 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]#[N:9])=[CH:3][CH:2]=1.[CH2:10](Br)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:8]#[N:9])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 10796Cesium carbonateHCID 41120852-(Pyridin-4-yl)acetonitrile

Product 1

HCID 20200552HCID 20200552, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Pyridylacetonitrile (1.18 g, 0.01 mole) dissolved in acetonitrile (20 ml) was heated under reflux with n-octyl bromide (1.73 ml, 0.01 mole) and caesium carbonate (4 g) for 1 hour, filtered and concentrated. Elution from a column of silica gel as described in Example 1 gave 2-(4-pyridyl)decanonitrile (1.58 g, 69% yield).

Workup

  1. temperaturewas heated
  2. filtrationfiltered
  3. concentrationconcentrated
  4. washElution from a column of silica gel

Sources & evidence

ORD record
ord-11229cb19341402492cc5891bae18820
Source dataset
uspto-grants-1987_05
Patent number
US04668689

Reaction notes

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