Benzyl Chloride → 1-Benzylcyclopropanecarbonitrile

HRID 2260409Notes

Reaction equation

HRID 2260409 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH:13]1([C:16]#[N:17])[CH2:15][CH2:14]1.[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.CCCCCC.O1CCCC1>[C:19]1([CH2:18][C:13]2([C:16]#[N:17])[CH2:15][CH2:14]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 7503Benzyl ChlorideHCID 7912DiisopropylamineHCID 79637CyclopropanecarbonitrileHCID 178418339Butyllithium

Product 1

HCID 223466521-BenzylcyclopropanecarbonitrileYield 53.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a mixture under nitrogen of 26.3 g (260 mmoles) of diisopropylamine and 300 ml of tetrahydrofuran cooled to -75° C., there is added dropwise 125 ml (200 mmoles) of n-butyllithium in a 1.6M hexane solution, then 13.4 g (200 mmoles) of commercial cyclopropanecarbonitrile and finally 25.3 g (200 mmoles) of benzyl chloride. The reaction mixture is stirred 2 hours at -70° C. then 2 days at 20° C. 4 ml of water is added, before washing the reaction mixture with water saturated with NaCl. The organic phase dried over Na2SO4 is concentrated to give a brown liquid, which is purified by distillation. There is obtained 16.8 g (yield=53.5%) of a colorless liquid. b.p.13 =140°-8° C.

Workup

  1. custom2 days
  2. customat 20° C
  3. washbefore washing the reaction mixture with water saturated with NaCl
  4. dry with materialThe organic phase dried over Na2SO4
  5. concentrationis concentrated
  6. customto give a brown liquid, which
  7. distillationis purified by distillation

Sources & evidence

ORD record
ord-8a9bf59cacfd4354b1d019c74408d29c
Source dataset
uspto-grants-1995_12
Patent number
US05476846

Reaction notes

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