Sodium Cyanide → 3,5-Difluoro-α-hydroxybenzeneacetonitrile

HRID 654410Notes

Reaction equation

HRID 654410 reaction equation
S(=O)(O)[O-].[Na+].[F:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([F:15])[CH:14]=1)[CH:10]=[O:11].[C-:16]#[N:17].[Na+]>O>[F:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([F:15])[CH:14]=1)[CH:10]([OH:11])[C:16]#[N:17]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 5881603,5-DifluorobenzaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 198871923,5-Difluoro-α-hydroxybenzeneacetonitrileYield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under stirring, 21 ml of a saturated aqueous solution of sodium bisulfite were added little by little to the mixture of 10.0 g of 3,5-difluorobenzaldehyde, 3.6 g of sodium cyanide and 15 ml of water. Upon the gradual addition, ice pieces were added at the same time to maintain the reaction temperature at 20°-30° C. The reaction mixture was stirred for 10 hours and then extracted with benzene. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure, whereby 10.2 g of crude 3,5-difluoromandelonitrile were obtained.

Workup

  1. additionUpon the gradual addition, ice pieces
  2. additionwere added at the same time
  3. temperatureto maintain the reaction temperature at 20°-30° C
  4. stirringThe reaction mixture was stirred for 10 hours
  5. extractionextracted with benzene
  6. washThe resulting organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76398a2498144985876a9623fc7111b9
Source dataset
uspto-grants-1992_07
Patent number
US05131947

Reaction notes

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