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

HRID 2172650Notes

Reaction equation

HRID 2172650 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-carbonitrileYield 90%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 4-bromo-3-fluorophenylacetonitrile (1 g, 4.6 mmoles) in toluene (4 ml) is mixed with 0.6 ml (7 mmoles) of 1,2-dibromoethane, a 50% NaOH aqueous solution (4 ml), and tetrabutylammonium bromide (0.32 g, 1 mmoles). The mixture is kept under stirring at room temperature for 4 hours, then diluted with water and extracted with ethyl acetate. The organic phase is recovered, and the solvent is eliminated under vacuum to give a brown solid, which is subjected to silica gel chromatography purification, to afford an orange to yellow product in the solid form (1 g, yield 90%).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is recovered
  3. customto give a brown solid, which
  4. customis subjected to silica gel chromatography purification
  5. customto afford an orange to yellow product in the solid form (1 g, yield 90%)

Sources & evidence

ORD record
ord-d9271eb63bc1495a98bc65d6de6fb0f6
Source dataset
uspto-grants-2015_06
Patent number
US09056818B2

Reaction notes

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