Hydrochloric Acid → 1-(4-BROMOPHENYL)CYCLOPENTANECARBONITRILE

HRID 2169267Notes

Reaction equation

HRID 2169267 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17]Br.Cl>CS(C)=O.CS(C)=O.CCOCC.O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:11]#[N:12])[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 27914Benzeneacetonitrile, 4-bromo-

Product 1

HCID 39876791-(4-BROMOPHENYL)CYCLOPENTANECARBONITRILEYield 89.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 19869614Ether dimethylsulfoxideSolvent

Procedure

To a suspension of NaH (2.55 g, 63.75 mmol, 60%) in dimethyl sulfoxide (50 mL) were added dropwise a mixture of 4-bromophenyl-acetonitrile (223) (5 g, 25.51 mmol) and 1,4-dibromobutane (3.04 mL, 25.51 mmol) dissolved in dimethyl sulfoxide:ether (1:1) (50 mL) at 0° C. and the reaction mixture was stirred at this temperature for 2 h. After completion of the reaction, water (20 mL) and 10% HCl solution (50 mL) were added to the mixture and the mixture was extracted with ethyl acetate (2×200 ml). The organic layer was dried over Na2SO4, concentrated and purified by 100-200 silica column chromatography using hexane as the eluent to give 1-(4-bromophenyl)-cyclopentanecarbonitrile (224) (5.7 g, 89%) as a white crystalline solid.

Workup

  1. additionwere added dropwise
  2. additionwere added to the mixture
  3. extractionthe mixture was extracted with ethyl acetate (2×200 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by 100-200 silica column chromatography

Sources & evidence

ORD record
ord-2972d98f6b774bfca9a73213d96d4d1d
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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