Dimethylformamide → HCID 12343269, compound

HRID 745272Notes

Reaction equation

HRID 745272 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]#[N:11].CN(C)C=O.[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][CH3:23]>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:20][CH2:21][CH2:22][CH3:23])[C:10]#[N:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 13655346(2,4-Dibromophenyl)acetonitrile

Product 1

HCID 12343269HCID 12343269, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred and cooled (ice-bath) mixture of 27.5 parts of 2,4-dibromobenzeneacetonitrile, 135 parts of N,N-dimethylformamide and 67.5 parts of benzene are added portionwise 3.2 parts of sodium hydride dispersion 78% while nitrogen gas is introduced. After stirring for one hour, 14 parts of 1-bromobutane are added dropwise. Upon completion, stirring is continued for 2 hours at room temperature. The reaction mixture is poured onto water and the product is extracted twice with 2,2'-oxybispropane. The combined extracts are washed twice with water, dried, filtered and evaporated. The residue is distilled, yielding 22 parts of 2,4-dibromo-α-butylbenzeneacetonitrile; bp. 124° C. at 0.05 mm. pressure.

Workup

  1. temperaturecooled
  2. additionis introduced
  3. stirringAfter stirring for one hour
  4. stirringUpon completion, stirring
  5. additionThe reaction mixture is poured onto water
  6. extractionthe product is extracted twice with 2,2'-oxybispropane
  7. washThe combined extracts are washed twice with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. distillationThe residue is distilled

Sources & evidence

ORD record
ord-d9f26a654af74aa5a10c42b856b09db9
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

Loading…