1,2-Dibromoethane → 1-(4-Bromo-3-fluorophenyl)cyclopropane-1-carbonitrile

HRID 1879433Notes

Reaction equation

HRID 1879433 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[F:11].Br[CH2:13][CH2:14]Br.[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:11]

Participants

7

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 116009532-(4-Bromo-3-fluorophenyl)acetonitrile

Product 1

HCID 117156671-(4-Bromo-3-fluorophenyl)cyclopropane-1-carbonitrile

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 4-bromo-3-fluorophenylacetonitrile (5 g, 23 mmoles) in toluene (20 ml) is added with 35 mmoles of 1,2-dibromoethane, a 50% NaOH aqueous solution (20 ml) and tetrabutylammonium bromide (1.6 g, 5 mmoles). The mixture is kept under stirring at room temperature for 5-12 hours, then diluted with water and extracted with ethyl acetate. The organic phase is washed with 1N HCl, then with brine, finally dried and concentrated under vacuum to give a brown solid, which is subjected to chromatography on a silica gel column (200 g), eluting with hexane-ethyl ether 1-1, to afford the product in the solid form.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with 1N HCl
  3. dry with materialwith brine, finally dried
  4. concentrationconcentrated under vacuum
  5. customto give a brown solid, which
  6. washeluting with hexane-ethyl ether 1-1
  7. customto afford the product in the solid form

Sources & evidence

ORD record
ord-9da71984f5df453bb3f30e8a5ecaa0c3
Source dataset
uspto-grants-2012_11
Patent number
US08314268B2

Reaction notes

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