Benzyl Bromide → 1-Benzylcyclopropanecarbonitrile

HRID 897390Notes

Reaction equation

HRID 897390 reaction equation
[CH:1]1([C:4]#[N:5])[CH2:3][CH2:2]1.C([N-]C(C)C)(C)C.[Li+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([C:1]1([C:4]#[N:5])[CH2:3][CH2:2]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 79637CyclopropanecarbonitrileHCID 2724682Lithium diisopropylamide

Product 1

HCID 223466521-Benzylcyclopropanecarbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of cyclopropyl cyanide (3.0 mL, 40 mmol) in 20 mL THF was dropwise added to a stirred, freshly prepared, mixture of lithium diisopropylamide (40 mmol) in THF (100 mL) at −78° C. After 30 min, a solution of benzyl bromide 7.8 mL, 60 mmol) in THF (20 mL) was dropwise added. The resulting mixture was warmed slowly over several hrs and stirred at rt 48 h. The reaction was quenched (250 mL saturated NH4Cl), extracted with ether (3×100 mL) and the combined organic extracts were dried (MgSO4), filtered and concentrated to afford a yellow oil.

Workup

  1. customfreshly prepared
  2. temperatureThe resulting mixture was warmed slowly over several hrs
  3. customThe reaction was quenched (250 mL saturated NH4Cl)
  4. extractionextracted with ether (3×100 mL)
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a yellow oil

Sources & evidence

ORD record
ord-d2626b5c39244cf09e8cd13fb09b5557
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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