Sodium hydride → 2-(2,3-Dichlorobenzyl)-3-oxopentanenitrile

HRID 510421Notes

Reaction equation

HRID 510421 reaction equation
[O:1]=[C:2]([CH2:6][CH3:7])[CH2:3][C:4]#[N:5].[H-].[Na+].Br[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=1[Cl:19]>CN(C=O)C>[Cl:19][C:13]1[C:14]([Cl:18])=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][CH:3]([C:2](=[O:1])[CH2:6][CH3:7])[C:4]#[N:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27346021-(Bromomethyl)-2,3-dichlorobenzeneHCID 99203693-Oxopentanenitrile

Product 1

HCID 712707892-(2,3-Dichlorobenzyl)-3-oxopentanenitrileYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-oxopentanenitrile (500 mg, 5.2 mmol) in DMF (10 mL) was added NaH (248 mg, 6.2 mmol) and stirred at 0° C. for 1 h. Then 1-(bromomethyl)-2,3-dichlorobenzene (1.23 g, 5.2 mmol) was added to the mixture and warmed to room temperature, stirred for 20 h. The mixture was concentrated under reduced pressure to give the crude titled product (1.2 g, 92%), which was used for next step without further purification.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 20 h
  3. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-af8b097b9b3b41349902c992cc9dea23
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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