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

HRID 1392699Notes

Reaction equation

HRID 1392699 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

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 500′ 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. temperaturewas heated to 500′ for 18 h
  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-45bbd659085248ab8f748c685878ef09
Source dataset
uspto-grants-2008_03
Patent number
US07342024B2

Reaction notes

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