Water → 2,2-Difluoro-1,3-benzodioxole-5-acetonitrile

HRID 870792Notes

Reaction equation

HRID 870792 reaction equation
Cl[CH2:2][C:3]1[CH:13]=[CH:12][C:6]2[O:7][C:8]([F:11])([F:10])[O:9][C:5]=2[CH:4]=1.[C-:14]#[N:15].[Na+].O.C(OC)(C)(C)C>CS(C)=O>[F:10][C:8]1([F:11])[O:7][C:6]2[CH:12]=[CH:13][C:3]([CH2:2][C:14]#[N:15])=[CH:4][C:5]=2[O:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 15413tert-Butyl methyl etherHCID 219928095-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole

Product 1

HCID 203113842,2-Difluoro-1,3-benzodioxole-5-acetonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
35 °C

Procedure

A solution of 5-chloromethyl-2,2-difluoro-1,3-benzodioxole (1 eq) in DMSO (1.25 vol) was added to a slurry of NaCN (1.4 eq) in DMSO (3 vol), while maintaining the temperature between 30 to 40° C. The mixture was stirred for 1 hour, and then water (6 vol) was added, followed by methyl tert-butyl ether (MTBE) (4 vol). After stirring for 30 minutes, the layers were separated. The aqueous layer was extracted with MTBE (1.8 vol). The combined organic layers were washed with water (1.8 vol), dried (Na2SO4), filtered, and concentrated to afford crude (2,2-difluoro-1,3-benzodioxol-5-yl)-acetonitrile (95%) that was used directly in the next step.

Workup

  1. stirringAfter stirring for 30 minutes
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with MTBE (1.8 vol)
  4. washThe combined organic layers were washed with water (1.8 vol)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-93bccef8ca7a4bd4995e1578d520da03
Source dataset
uspto-grants-2015_03
Patent number
US08969574B2

Reaction notes

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