1,4-Dibromobutane → 1-(4-BROMOPHENYL)CYCLOPENTANECARBONITRILE

HRID 2366569Notes

Reaction equation

HRID 2366569 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15]Br.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 27914Benzeneacetonitrile, 4-bromo-HCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 39876791-(4-BROMOPHENYL)CYCLOPENTANECARBONITRILE

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-bromophenyl)acetonitrile (1.0 g, 5.10 tntnol) and 1,4-dibromobutane (0.67 ml, 5.6 mmol) in THF (10 ml) was added potassium bis(trimethylsilyl) amide (2.23 g, 11.2 mmol) and tetra-n-butylammonium bromide (164 mg, 0.51 mmol). The mixture was stirred for 2 h and then quenched with 1N HCl. Ethyl acetate was added, the layers separated and the organic layer was washed with water and brine. Drying, solvent evaporation and flash chromatography (silica gel, 20% EtOAc/hexanes) gave 1-(4-bromophenyl)cyclopentanecarbonitrile.

Workup

  1. customquenched with 1N HCl
  2. additionEthyl acetate was added
  3. customthe layers separated
  4. washthe organic layer was washed with water and brine
  5. customDrying
  6. customsolvent evaporation and flash chromatography (silica gel, 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-903a9014c1bb4be8a7eabac0fc306023
Source dataset
uspto-grants-2014_04
Patent number
US08697863B2

Reaction notes

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