Benzyl Bromide → 2-butyl-2-phenylhexanenitrile

HRID 1969366Notes

Reaction equation

HRID 1969366 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C(Br)[C:13]1[CH:18]=[CH:17][CH:16]=CC=1>O1CCCC1>[CH2:8]([C:1]([CH2:13][CH2:18][CH2:17][CH3:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]#[N:9])[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

Product 1

HCID 2367002-butyl-2-phenylhexanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flame dried 500 ml three neck round bottomed flask, equipped with a dry argon inlet, magnetic stir bar, and thermometer, is added benzyl cyanide ((1), 5.0 gm.; 0.043 mol) and tetrahydrofuran (100 ml). To the reaction is slowly added sodium hydride (60% in oil) (7.2 gm, 0.1075 mol) over one hour. Once addition is complete the reaction is stirred at room temperature for 1 hour. To the reaction is added benzyl bromide (18.4 gm; 0.043 mol) and the reaction is stirred at 50° C. for 18 hours. The reaction is evaporated to dryness, residue dissolved in toluene and washed with 1N HCl. Organic phase is dried with Na2SO4, filtered and evaporated to yield α,α-dibutyl-benzeneacetonitrile (2), wt=7.7 gm (65%).

Workup

  1. dry with materialTo a flame dried 500 ml three neck round bottomed flask
  2. customequipped with a dry argon inlet, magnetic stir bar
  3. customover one hour
  4. additionOnce addition
  5. stirringthe reaction is stirred at 50° C. for 18 hours
  6. customThe reaction is evaporated to dryness, residue
  7. dissolutiondissolved in toluene
  8. washwashed with 1N HCl
  9. dry with materialOrganic phase is dried with Na2SO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-81565c542c7e4f9c8a73cc3e4179e056
Source dataset
uspto-grants-2013_04
Patent number
US08426596B2

Reaction notes

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