1-Bromo-2-Chloroethane → 1-(2,2-Difluorobenzo[D][1,3]dioxol-5-YL)cyclopropanecarbonitrile

HRID 45278

Reaktionsgleichung

Reaktionsgleichung von HRID 45278
[OH-].[Na+].[F:3][C:4]1([F:18])[O:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]3([C:16]#[N:17])[CH2:15][CH2:14]3)=[CH:12][C:6]=2[O:5]1.FC1(F)OC2C=CC(CC#N)=CC=2O1.BrCCCl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[F:18][C:4]1([F:3])[O:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]3([C:16]#[N:17])[CH2:15][CH2:14]3)=[CH:12][C:6]=2[O:5]1

Komponenten

6

Edukt 3

HCID 78491-Bromo-2-ChloroethaneHCID 203113842,2-Difluoro-1,3-benzodioxole-5-acetonitrileHCID 673151521-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonitrile Sodium hydroxide

Produkt 1

HCID 574461501-(2,2-Difluorobenzo[D][1,3]dioxol-5-YL)cyclopropanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonitrile Sodium hydroxide (50% aqueous solution, 10 mL) was slowly added to a mixture of crude (2,2-difluoro-benzo[1,3]dioxol-5-yl)-acetonitrile, benzyltriethylammonium chloride (3.00 g, 15.3 mmol), and 1-bromo-2-chloroethane (4.9 g, 38 mmol) at 70° C. The mixture was stirred overnight at 70° C. and the reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated to dryness to give crude 1-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonitrile, which was used directly in the next step.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-7ed85289fe0e4e46950710b1bf82c8b3
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541453B2

Verknüpfte Notizen

Wird geladen…