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

HRID 39445

Reaktionsgleichung

Reaktionsgleichung von HRID 39445
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 203113842,2-Difluoro-1,3-benzodioxole-5-acetonitrileAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-23859e6ff6fb470a8830acf3e5d16818
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524910B2

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