Sodium Cyanide → 2,3-Dichloro-4-methoxybenzeneacetonitrile

HRID 1280324Notes

Reaction equation

HRID 1280324 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH2:4]Br.[C-:13]#[N:14].[Na+]>CS(C)=O>[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH2:4][C:13]#[N:14]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 11821665HCID 11821665, compound

Product 1

HCID 184250332,3-Dichloro-4-methoxybenzeneacetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

With stirring, a solution of 68 g of 2,3-dichloro-4-methoxybenzyl bromide in 220 ml of dimethyl sulfoxide was added dropwise to a suspension of 15 g of anhydrous sodium cyanide in 250 ml of anhydrous dimethyl sulfoxide. The mixture was subsequently heated to reflux temperature under an atmosphere of nitrogen for 5 hours. The cold reaction mixture was poured into 1.5 l of ice-water, after which the solid product which had formed was separated off, washed with water and purified by trituration with petroleum ether (at 40—60° C). Yield: 51 g (white crystals); m.p.: 118—119° C.

Workup

  1. temperatureThe mixture was subsequently heated
  2. temperatureto reflux temperature under an atmosphere of nitrogen for 5 hours
  3. customThe cold reaction mixture
  4. customafter which the solid product which had formed
  5. customwas separated off
  6. washwashed with water
  7. custompurified by trituration with petroleum ether (at 40—60° C)

Sources & evidence

ORD record
ord-2198a65cd1b34a10bd8ceeed17b8dbd4
Source dataset
uspto-grants-2002_09
Patent number
US06451734B1

Reaction notes

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