Sodium Cyanide → 2,2-Difluoro-1,3-benzodioxole-5-acetonitrile

HRID 1505074Notes

Reaction equation

HRID 1505074 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+]>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

4

Reactant 2

HCID 8929Sodium CyanideHCID 219928095-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole

Product 1

HCID 203113842,2-Difluoro-1,3-benzodioxole-5-acetonitrileYield 78.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of crude 5-chloromethyl-2,2-difluoro-benzo[1,3]dioxole (4.4 g) and sodium cyanide (1.36 g, 27.8 mmol) in dimethylsulfoxide (50 mL) was stirred at room temperature overnight. The reaction mixture was poured into ice and extracted with ethyl acetate (300 mL). The organic layer was dried over sodium sulfate and evaporated to dryness to give crude (2,2-difluoro-benzo[1,3]dioxol-5-yl)-acetonitrile (3.3 g) which was used directly in the next step.

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted with ethyl acetate (300 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-44aecbd4eb714bdc9cad4094a678ae20
Source dataset
uspto-grants-2015_12
Patent number
US09216969B2

Reaction notes

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