Bromoacetonitrile → Methyl 2-(cyanomethyl)-2-methylbutanoate

HRID 1108364Notes

Reaction equation

HRID 1108364 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

HCID 11534BromoacetonitrileHCID 13357Methyl 2-methylbutyrateHCID 2724682Lithium diisopropylamide

Product 1

HCID 10820797Methyl 2-(cyanomethyl)-2-methylbutanoateYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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).

Workup

  1. customas described above in the preparation of Example 1
  2. customgave 16.57 g of the crude product as a dark colored liquid
  3. distillationdistilled

Sources & evidence

ORD record
ord-63a25fedce88442fa5f9e113d40f3cd4
Source dataset
uspto-grants-2000_05
Patent number
US06066666

Reaction notes

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