Isobutyronitrile → 5-chloro-2,2-dimethylpentanenitrile

HRID 1699122Notes

Reaction equation

HRID 1699122 reaction equation
[C:1](#[N:5])[CH:2]([CH3:4])[CH3:3].C[N-]C.[Li+].Br[CH2:11][CH2:12][CH2:13][Cl:14]>CCCCCC>[Cl:14][CH2:13][CH2:12][CH2:11][C:2]([CH3:4])([CH3:3])[C:1]#[N:5]

Participants

5

Reactant 3

HCID 6559IsobutyronitrileHCID 80061-Bromo-3-chloropropaneHCID 5152226Lithium N-methylmethanaminide

Product 1

HCID 2642175-chloro-2,2-dimethylpentanenitrileYield 90.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Isobutyronitrile (9.9 g, 0.143 mole) is added dropwise to a suspension of lithium dimethylamide (7.3 g, 0.143 mole) in hexanes. The resultant anion solution is added to a solution of 1-bromo-3-chloropropane (24.8 g, 0.16 mole) in hexane at 5° to 10° C., warmed to room temperature, and quenched with water. The phases are separated and the organic phase is concentrated in vacuo to afford the title product as a yellow oil, 19.0 g(80% pure, 90.9% 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-42f35317122a4384aeca28ae6872a921
Source dataset
uspto-grants-2002_02
Patent number
US06344580B1

Reaction notes

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