1,2-Dibromoethane → 1-(Biphenyl-4-YL)-cyclopropanecarbonitrile

HRID 2391043Notes

Reaction equation

HRID 2391043 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Br[CH2:19][CH2:20]Br.CCOC(C)=O>O.C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=[CH:11][C:10]([C:13]2([C:14]#[N:15])[CH2:20][CH2:19]2)=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 358564-Biphenylacetonitrile

Product 1

HCID 666605281-(Biphenyl-4-YL)-cyclopropanecarbonitrileYield 99.4%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

4-phenyl-phenylacetonitrile (VWR scientific, 55.7 g, 289 mmol) was added to a solution of KOH (161.6 g, 2890 mmol) in water (170 mL) and toluene (550 mL) at room temperature. Tetrabutyl ammonium bromide (9.2 g, 29 mmol) followed by 1,2 dibromoethane (64.9 g, 347 mmol) were added and the solution was heated to 65° C. overnight. Reaction complete by TLC (10% EtOAc/hex). The organic layer was extracted 2 times with dilute hydrochloric acid, dried and evaporated to yield 63 g of 1-(biphenyl-4-yl)cyclopropanecarbonitrile.

Workup

  1. additionwere added
  2. extractionThe organic layer was extracted 2 times with dilute hydrochloric acid
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-75f7980b7f1f424e896a688be11f4e0f
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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