Water → 4-(2-Fluorophenyl)butanenitrile

HRID 355952Notes

Reaction equation

HRID 355952 reaction equation
[O-][C:2]#[N:3].[Na+].S(C1C=CC(C)=CC=1)(O[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])(=O)=O.O>CS(C)=O>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][CH2:10][CH2:9][C:2]#[N:3]

Participants

5

Reactant 3

HCID 962WaterHCID 517096Sodium CyanateHCID 224494783-(2-Fluorophenyl)propyl 4-methylbenzenesulfonate

Product 1

HCID 224495394-(2-Fluorophenyl)butanenitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a solution of 9.89 gm of sodium cyanate in 35 ml of dimethylsulfoxide (hereinafter abbreviated as DMSO) was added dropwise a solution of 31.2 gm of the compound prepared in (4) above in 70 ml of DMSO. The mixture was stirred for 12 hours at room temperature. After the addition of 500 ml of water, the mixture was extracted twice with 200 ml of ether. The extract was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 15.4 gm of the title compound.

Workup

  1. extractionthe mixture was extracted twice with 200 ml of ether
  2. washThe extract was washed with water and saturated brine in this order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-189b92644c2542b29863f80c1aedef42
Source dataset
uspto-grants-1998_11
Patent number
US05834476

Reaction notes

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