Water → (2-Methoxy-5-nitrophenyl)acetonitrile

HRID 898152Notes

Reaction equation

HRID 898152 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:4]=1[CH2:5]Br.[C-:14]#[N:15].[Na+].O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:4]=1[CH2:5][C:14]#[N:15]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 775162-(Bromomethyl)-1-methoxy-4-nitrobenzene

Product 1

HCID 12701835(2-Methoxy-5-nitrophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-methoxy-5-nitrobenzyl bromide (984 mg) in dimethylsulfoxide (5 mL) was added sodium cyanide (216 mg) and the mixture was stirred at 80 degrees for 10 minutes. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous sodium sulfate, and concentrated to give the title compound having the following physical data. The obtained title compound was used to next reaction without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5428e35170f14bcbb065c10e7cff4aff
Source dataset
uspto-grants-2008_04
Patent number
US07351705B2

Reaction notes

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