Potassium Carbonate → 2-(4-Bromophenyl)propanenitrile

HRID 1167202Notes

Reaction equation

HRID 1167202 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[C:11](=O)([O-])[O-].[K+].[K+]>C(=O)(OC)OC.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 27914Benzeneacetonitrile, 4-bromo-

Product 1

HCID 107509272-(4-Bromophenyl)propanenitrileYield 1,498.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 12021Dimethyl CarbonateSolvent

Procedure

A solution of 50.0 g (225.0 mmol) of 4-bromophenyl-acetonitrile and 1.8 g (12.8 mmol) of potassium carbonate in 387 mL of dimethyl carbonate was heated to 180° C. in a sealed vessel for 16 hours. The solution was then cooled, diluted with 200 mL of ethyl acetate and washed once with 100 mL water, once with 100 mL of 10% aqueous sodium bisulfate and once with 100 mL brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. The residue was distilled under vacuum through a short path distillation apparatus to afford 40.3 g (85%) of the title compound.

Workup

  1. temperatureThe solution was then cooled
  2. washwashed once with 100 mL water, once with 100 mL of 10% aqueous sodium bisulfate and once with 100 mL brine
  3. dry with materialThe organic portion was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. distillationThe residue was distilled under vacuum through a short path distillation apparatus

Sources & evidence

ORD record
ord-ebcfbe5c94374af1b57e233f61da09a7
Source dataset
uspto-grants-2003_09
Patent number
US06617351B1

Reaction notes

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