1-Bromo-2-Chloroethane → 1-(3-Methylphenyl)cyclopropane-1-carbonitrile

HRID 2170716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2170716
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]#[N:9])[CH:2]=1.[OH-].[Na+].Br[CH2:14][CH2:15]Cl>C1(C)C=CC=CC=1.O>[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([C:8]#[N:9])[CH2:15][CH2:14]2)[CH:2]=1

Komponenten

6

Edukt 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 76279m-Methylphenylacetonitrile

Produkt 1

HCID 200261921-(3-Methylphenyl)cyclopropane-1-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of 2-(m-tolyl)acetonitrile (4.2 g, 32 mmol) in toluene (15 mL) was added sodium hydroxide (30 mL, 50% w/w in water, 375 mmol), 1-bromo-2-chloroethane (9.3 mL, 112 mmol) and (n-Bu)4Br (0.5 g, 1.55 mmol). The mixture was heated at 60° C. overnight. After cooling to room temperature, the reaction mixture was diluted with water (40 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure and purified by silica gel chromatography to obtain the title compound.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6684f7a224ba4610bd72a6910d63fa99
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051265B2

Notizen zur Reaktion

Wird geladen…