N-bromobutanimide → 2-(4-Bromo-3-cyanomethyl-phenyl)-2-methylpropionitrile

HRID 406382Notes

Reaction equation

HRID 406382 reaction equation
Br[N:2]1C(=O)CC[C:3]1=O.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:20])([CH3:19])[C:17]#[N:18])=[CH:12][C:11]=1[CH3:21]>C(Cl)(Cl)(Cl)Cl>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:19])([CH3:20])[C:17]#[N:18])=[CH:12][C:11]=1[CH2:21][C:3]#[N:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 582984722-(4-Bromo-3-methylphenyl)-2-methylpropanenitrile

Product 1

HCID 666187122-(4-Bromo-3-cyanomethyl-phenyl)-2-methylpropionitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-bromosuccinimide (1.04 g) and 2,2′-azobis(isobutylnitrile) (30 mg) were added to the carbon tetrachloride solution (7 ml) of 2-(4-bromo-3-methylphenyl)-2-methylpropionitrile (1.26 g) and then the solution was refluxed with heating for an hour. The solution was cooled on ice, then after removing the insoluble substances by filtration, the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in ethanol (10 ml) and water (1 ml) and a solution of potassium cyanide (0.41 g) was added to the solution. The reaction mixture was stirring overnight at room temperature. To the reaction mixture was added the ice-cold water and ethyl acetate, and the organic layer was separated. The obtained organic layer was sequentially washed with water (twice) and brine. After drying over anhydrous magnesium sulfate, the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier; Wakogel™ C-200; elution solvent; heptane:ethyl acetate, 19:1→5:1) to obtain the title compound. (917 mg) The property values of the obtained compound are as follows; 1H-NMR (CDCl3) δ (ppm): 1.74 (s, 6H), 3.87 (s, 2H), 7.38 (dd, J=8.4, 2.4 Hz, 1H), 7.57 (d, J=2.4 Hz, 1H), 7.64 (d, J=8.4 Hz, 1H).

Workup

  1. temperaturethe solution was refluxed
  2. temperaturewith heating for an hour
  3. temperatureThe solution was cooled on ice
  4. customafter removing the insoluble substances
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. dissolutionThe obtained residue was dissolved in ethanol (10 ml)
  8. additionwater (1 ml) and a solution of potassium cyanide (0.41 g) was added to the solution
  9. additionTo the reaction mixture was added the ice-cold water and ethyl acetate
  10. customthe organic layer was separated
  11. washThe obtained organic layer was sequentially washed with water (twice) and brine
  12. dry with materialAfter drying over anhydrous magnesium sulfate
  13. concentrationthe organic layer was concentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (carrier; Wakogel™ C-200; elution solvent; heptane:ethyl acetate, 19:1→5:1)

Sources & evidence

ORD record
ord-051d507906e44afa82bfaee11ac89e75
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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