Sodium Cyanide → 3-Chloro-5-(trifluoromethoxy)phenylacetonitrile

HRID 1990732Notes

Reaction equation

HRID 1990732 reaction equation
S(O[CH2:6][C:7]1[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[C:9]([Cl:18])[CH:8]=1)(=O)(=O)C.[C-:19]#[N:20].[Na+]>CS(C)=O>[Cl:18][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=1)[CH2:6][C:19]#[N:20]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 219046353-Chloro-5-trifluoromethoxybenzyl mesylate

Product 1

HCID 219046503-Chloro-5-(trifluoromethoxy)phenylacetonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-chloro-5-trifluoromethoxybenzyl mesylate (8.2 g, 26.8 mmol; see step (i) above) in DMSO (50 mL) was added sodium cyanide (2.6 g, 53.6 mmol). The resulting heterogeneous solution was warmed to 50° C. and sonicated for 1 hour. The reaction was cooled and partitioned between Et2O and H2O. The organics were washed with H2O (2×) and brine (2×). The combined aqueous phases were extracted with Et2O (1×). The combined organics were dried (Na2SO4), filtered and concentrated under a low heat and partial vacuum to afford the sub-title compound (6.3 g, 100%) as a reddish volatile oil which was used in the next step without further purification.

Workup

  1. customsonicated for 1 hour
  2. temperatureThe reaction was cooled
  3. custompartitioned between Et2O and H2O
  4. washThe organics were washed with H2O (2×) and brine (2×)
  5. extractionThe combined aqueous phases were extracted with Et2O (1×)
  6. dry with materialThe combined organics were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under
  9. temperaturea low heat

Sources & evidence

ORD record
ord-b44654fe9a19441086df788513669ef8
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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