Isobutyronitrile → 5-chloro-2,2-dimethylpentanenitrile

HRID 1699121Notes

Reaction equation

HRID 1699121 reaction equation
[C:1](#[N:5])[CH:2]([CH3:4])[CH3:3].Br[CH2:7][CH2:8][CH2:9][Cl:10].C[Si]([NH-])(C)C.C[Si]([NH-])(C)C.[Li+].[Li+]>>[Cl:10][CH2:9][CH2:8][CH2:7][C:2]([CH3:4])([CH3:3])[C:1]#[N:5]

Participants

4

Reactant 3

HCID 6559IsobutyronitrileHCID 80061-Bromo-3-chloropropaneHCID 86588160Lithim bis(trimethylsilylamide)

Product 1

HCID 2642175-chloro-2,2-dimethylpentanenitrileYield 85.7%

Conditions

Temperature
69 °C

Procedure

Isobutyronitrile (13.8 g, 0.20 mole), and 1-bromo-3-chloropropane (34.5 g, 0.22) are added sequentially to a stirred 1 M solution of lithium bis(trimethylsilylamide) (200 ml, 0.20 mole) in hexanes, stirred for two hours at 69° C. and quenched with water. The phases are separated and the organic phase is concentrated in vacuo to afford the title product as an oil, 38.9 g (64% pure, 85.7% yield), identified via gas chromatography.

Workup

  1. customquenched with water
  2. customThe phases are separated
  3. concentrationthe organic phase is concentrated in vacuo

Sources & evidence

ORD record
ord-97d6f263422f4006a915efcf8857fb7e
Source dataset
uspto-grants-2002_02
Patent number
US06344580B1

Reaction notes

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