Hydrochloric Acid → 2-Chloro-3-(2,6-dibromophenyl)propanenitrile

HRID 657534Notes

Reaction equation

HRID 657534 reaction equation
N(OC(C)(C)C)=O.[C:8](#[N:11])[CH:9]=[CH2:10].[Br:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[C:14]=1N.[ClH:21]>C(#N)C>[Br:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[C:14]=1[CH2:10][CH:9]([Cl:21])[C:8]#[N:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7855AcrylonitrileHCID 10906Tert-Butyl nitriteHCID 690982,6-Dibromoaniline

Product 1

HCID 685330422-Chloro-3-(2,6-dibromophenyl)propanenitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To 62.4 g (464 mmol/1.2 eq.) of cupric chloride, 76 mL (580 mmol/1.5 eq.) of tert-butyl nitrite and 483 mL (7.34 moles/19 eq.) of acrylonitrile in 475 mL of acetonitrile, at ambient temperature, there is poured, dropwise, over 1 hour, 100 g (386 mmol) of 2,6-dibromoaniline dissolved in 380 mL of acetonitrile. Stirring is carried out for a further 1 hour at ambient temperature, and then the reaction mixture is poured into 1 liter of 20% aqueous hydrochloric acid solution. The aqueous phase is extracted with toluene and the combined toluene phases are washed with aqueous saturated sodium chloride solution. After concentration, the desired product is obtained and used as such in the following Step.

Workup

  1. waitis carried out for a further 1 hour at ambient temperature
  2. extractionThe aqueous phase is extracted with toluene
  3. washthe combined toluene phases are washed with aqueous saturated sodium chloride solution
  4. concentrationAfter concentration

Sources & evidence

ORD record
ord-cb47db6c63c84518ab55de1138953d43
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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