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

HRID 861024Notes

Reaction equation

HRID 861024 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13]Cl.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:13][CH2:12]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 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (4-bromo-phenyl)-acetonitrile (1.0 eq.), 1-bromo-2-chloro-ethane (1.6 eq.), triethylbenzyl ammonium chloride (0.03 eq.) and aqueous NaOH 50% (6 eq.) was stirred for 12 h at 60° C. The resulting mixture was poured in water and extracted with Et2O (2×). The combined organic extracts were washed with HCl 5%, brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 95:5) afforded the title compound as a foam.

Workup

  1. extractionextracted with Et2O (2×)
  2. washThe combined organic extracts were washed with HCl 5%, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b4642c4f852a4db180f572f2cc73b8d8
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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