Bromoacetonitrile → Methyl 2-(cyanomethyl)-2-methylbutanoate
Reaction equation
[CH3:1][CH:2]([CH2:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4].Br[CH2:10][C:11]#[N:12].C([N-]C(C)C)(C)C.[Li+]>C1COCC1>[C:11]([CH2:10][C:2]([CH3:1])([CH2:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4])#[N:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The reaction of methyl 2-methylbutyrate (13.34 g, 115 mmol) with bromoacetonitrile (16.56 g, 138 mmol) in the presence of lithium diisopropylamide (prepared by treating diisopropylamine (12.78 g, 126.5 mmol) with butyllithium in hexanes (2.5 M, 50.6 mL, 126.5 mmol)) in THF (175 mL), as described above in the preparation of Example 1, gave 16.57 g of the crude product as a dark colored liquid. The crude product was vacuum distilled to give the nitrile (10.85 g, 61%) as a colorless liquid: bp 83-85° C. (10 mmHg).