Diethyl Ether → 1-(3,4-Dichlorophenyl)cyclopentanecarbonitrile

HRID 266884Notes

Reaction equation

HRID 266884 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5]Br.[Cl:7][C:8]1[CH:9]=[C:10]([CH2:15][C:16]#[N:17])[CH:11]=[CH:12][C:13]=1[Cl:14].[OH-].[Na+].CCOCC>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2([C:16]#[N:17])[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 80561,4-DibromobutaneHCID 14798Sodium HydroxideHCID 76690(3,4-Dichlorophenyl)acetonitrile

Product 1

HCID 212584761-(3,4-Dichlorophenyl)cyclopentanecarbonitrile

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

1,4-Dibromobutane (106 ml) was added dropwise over 1 hour at 70°-80° C. under nitrogen to a stirred mixture of 3,4-dichlorophenylacetonitrile (150 g) , benzyltriethylammonium chloride (2 g) and 50% aqueous sodium hydroxide solution (300 ml). When the addition was complete the mixture was stirred at 70°-80° C. for 2 hours, then cooled to ambient temperature. Ether (400 ml) and water (200 ml) were added and the layers were separated. The aqueous layer was washed with ether (2×200 ml), then the combined organic solutions were dried over magnesium sulphate and the solvent removed in vacuo. The residue was distilled to give 1-(3,4-dichlorophenyl)cyclopentanecarbonitrile as a pale yellow oil (135 g), b.p. 132°-140° C./0.4 mbar.

Workup

  1. additionWhen the addition
  2. customthe layers were separated
  3. washThe aqueous layer was washed with ether (2×200 ml)
  4. dry with materialthe combined organic solutions were dried over magnesium sulphate
  5. customthe solvent removed in vacuo
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-c5940622b1a148008fe8eb76d908fa8c
Source dataset
uspto-grants-1997_07
Patent number
US05652271

Reaction notes

Loading…