Sodium Cyanide → 3-(3-Methoxyphenyl)propanenitrile

HRID 337253Notes

Reaction equation

HRID 337253 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[CH:5]=1.[C-:12]#[N:13].[Na+]>CN(C=O)C>[CH3:11][O:10][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][C:12]#[N:13])[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 1374501-Bromo-2-(3-methoxyphenyl)ethane

Product 1

HCID 100348983-(3-Methoxyphenyl)propanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of 1-(2-bromoethyl)-3-methoxybenzene (10 g, 46.4 mmol), NaCN (2.73 g, 55.8 mmol) in dry DMF (20 ml) was heated at 90° C. for 6 hours or until all the starting material is consumed, the reaction was cooled, diluted with EtOAc (60 ml) and washed with water (20 ml×3), brine, the organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound as an oil.

Workup

  1. customis consumed
  2. temperaturethe reaction was cooled
  3. additiondiluted with EtOAc (60 ml)
  4. washwashed with water (20 ml×3), brine
  5. dry with materialthe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

Sources & evidence

ORD record
ord-e22d56c35a134581921923f5e5275be0
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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