1-Bromo-2-Chloroethane → 1-(4-Bromophenyl)Cyclopropanecarbonitrile

HRID 2246784Notes

Reaction equation

HRID 2246784 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:14][CH2:15]Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 27914Benzeneacetonitrile, 4-bromo-

Product 1

HCID 27952731-(4-Bromophenyl)Cyclopropanecarbonitrile

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

To a room temperature solution of 4-bromophenylacetonitrile (18.0 g) in a solution of 22 mL of sodium hydroxide (50% in water W/W) were added 1-bromo-2-chloroethane and (2.0 mL) and benzyltriethylammonium chloride (627 mg). The mixture was heated at 60° C. overnight. The reaction mixture was cooled to room temperature and diethyl ether was added (300 mL) and partitioned. The ether layer was washed with water (100 mL), hydrogen chloride (100 mL, 10% HCl in water) and brine. Then dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by swish using diethyl ether and hexanes to yield the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned
  3. washThe ether layer was washed with water (100 mL), hydrogen chloride (100 mL, 10% HCl in water) and brine
  4. dry with materialThen dried with magnesium sulfate
  5. customthe solvent removed in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-defc3bb75698410da119f75ac8a86ae9
Source dataset
uspto-grants-2010_03
Patent number
US07687524B2

Reaction notes

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