N-bromobutanimide → Bromo-pivaloylacetonitrile

HRID 2384465Notes

Reaction equation

HRID 2384465 reaction equation
[C:1]([CH2:7][C:8]#[N:9])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:10][CH:7]([C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[C:8]#[N:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 11586483Bromo-pivaloylacetonitrileYield 87.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Pivaloylacetonitrile (1.00 g, 7.99 mmol) was dissolved in carbon tetrachloride (15 mL). N-Bromosuccinimide (1.42 g, 7.99 mmol) was added, and the mixture was refluxed for 15 minutes. After cooling, the insoluble matter was filtered off, and the residue obtained by evaporation of the filtrate under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give the title compound (1.43 g, 87.9%) as a yellowish brown oil.

Workup

  1. temperaturethe mixture was refluxed for 15 minutes
  2. temperatureAfter cooling
  3. filtrationthe insoluble matter was filtered off
  4. customthe residue obtained by evaporation of the filtrate under reduced pressure
  5. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-9fac9ba62bf54ebbbec92822c636fda5
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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