Water → 2-(2-Fluoro-3-methoxyphenyl)acetonitrile

HRID 1443145Notes

Reaction equation

HRID 1443145 reaction equation
[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[C-:12]#[N:13].[Na+].O>CS(C)=O>[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][C:12]#[N:13]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 538708331-(Chloromethyl)-2-fluoro-3-methoxybenzene

Product 1

HCID 230744722-(2-Fluoro-3-methoxyphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

24.89 g (142.56 mmol) of 2-fluoro-3-methoxybenzyl chloride is stirred in 200 ml of DMSO with 8.38 g (171.07 mmol) of sodium cyanide for three hours at 90° C. The reaction mixture is poured into water and extracted four times with methyl tert-butyl ether. The combined organic phases are washed with brine, dried, the desiccant is suctioned off, and the solvent is spun off. First, only a portion of the residue (21.43 g) is incorporated in crude form into the next stage.

Workup

  1. extractionextracted four times with methyl tert-butyl ether
  2. washThe combined organic phases are washed with brine
  3. customdried

Sources & evidence

ORD record
ord-f6adfd2c55e64517aed0b9c41f347bd7
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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