Hydrochloric Acid → 1-(4-Nitrophenyl)cyclopropanecarbonitrile

HRID 887622Notes

Reaction equation

HRID 887622 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]#[N:14])=[CH:8][CH:7]=1)([O-:5])=[O:4].Br[CH2:16][CH2:17]Br.Cl>O.[Cl-].C([N+](CC)(CC)CC)C.C(Cl)Cl>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2([C:13]#[N:14])[CH2:17][CH2:16]2)=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 68386p-Nitrophenylacetonitrile

Product 1

HCID 43990411-(4-Nitrophenyl)cyclopropanecarbonitrile

Reagents, catalysts & solvents 2

HCID 16211205Tetraethylammonium chloride monohydrateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

NaOH (5.0 N, 80 ml) was added to a mixture of 4-nitrophenylacetonitrile (10.0 g, 61.7 mmol), 1,2-dibromoethane (8.0 ml, 92.5 mmol), and tetraethylammonium chloride hydrate (10.2 g, 61.7 mmol) in 200 ml of CH2Cl2 at RT. The resulting mixture was stirred at RT for 24 h, diluted with CH2Cl2, and acidified with HCl (10%, aq). The organic layer was separated, washed with brine, condensed, and the crude was purified by flash column chromatography. The titled compound was obtained as a light yellowish solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine, condensed
  3. customthe crude was purified by flash column chromatography

Sources & evidence

ORD record
ord-8d0f26cb5efc4c358b41fc475b0b3f38
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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