Methanol → 2,3-Dichloro-4-methoxybenzeneacetonitrile

HRID 1497502Notes

Reaction equation

HRID 1497502 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([Cl:11])[C:4]=1[Cl:12].O.CO.[C-:16]#[N:17].[Na+]>CS(C)=O>[Cl:12][C:4]1[C:5]([Cl:11])=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[CH2:2][C:16]#[N:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8929Sodium CyanideHCID 11821665HCID 11821665, compound

Product 1

HCID 184250332,3-Dichloro-4-methoxybenzeneacetonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 1-(bromomethyl)-2,3-dichloro-4-methoxybenzene (1.00 g), water (3.00 mL), methanol (6.00 mL), and dimethyl sulfoxide (2.00 mL) was added sodium cyanide (246 mg) at room temperature, followed by stirring at 40° C. for 5 hours. The reaction mixture was concentrated under reduced pressure, and then water was added thereto. The resulting solid was collected by filtration to obtain (2,3-dichloro-4-methoxyphenyl)acetonitrile (776 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionwater was added
  3. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-fb58c336ff384cbcacf98078eb47cd9a
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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