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

HRID 1294369Notes

Reaction equation

HRID 1294369 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[CH2:11](Cl)[CH2:12]Br>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 78491-Bromo-2-ChloroethaneHCID 27914Benzeneacetonitrile, 4-bromo-

Product 1

HCID 27952731-(4-Bromophenyl)Cyclopropanecarbonitrile

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-bromophenylacetonitrile (1 eq), 1,2-bromochloroethane (1.5 eq), benzyltriethylammonium chloride (0.14 eq) in NaOH 50% (4M) was heated to 50° C. for 18 h. The mixture was cooled to rt, quenched with HCl 5% and diluted with ether. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (hexane:EtOAc, 95:5) afforded the title compound.

Workup

  1. temperatureThe mixture was cooled to rt
  2. customquenched with HCl 5%
  3. additiondiluted with ether
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e5db06ee9fcf4813967a8fdcb1545434
Source dataset
uspto-grants-2007_07
Patent number
US07238706B2

Reaction notes

Loading…