1-Bromo-3-chloropropane → 5-Chloro-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile

HRID 979380

Reaktionsgleichung

Reaktionsgleichung von HRID 979380
[CH:1]([CH:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)[C:5]#[N:6])([CH3:3])[CH3:2].[NH2-].[Na+].Br[CH2:20][CH2:21][CH2:22][Cl:23]>C1(C)C=CC=CC=1>[CH3:16][O:15][C:9]1[CH:8]=[C:7]([C:4]([CH:1]([CH3:3])[CH3:2])([CH2:20][CH2:21][CH2:22][Cl:23])[C:5]#[N:6])[CH:12]=[CH:11][C:10]=1[O:13][CH3:14]

Komponenten

5

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 24533Sodium amideHCID 893962-(3,4-Dimethoxyphenyl)-3-methylbutanenitrile

Produkt 1

HCID 6199535-Chloro-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

A solution of 2-(3,4-dimethoxyphenyl)-2-isopropylacetonitrile (6a) in toluene is slowly added to sodium amide (1.5 eq) in toluene, and the resulting mixture warmed to 80°-90° C. for one hour. The mixture was then cooled to 15° C. and 1-bromo-3-chloropropane (2 eq) slowly added and stirred for two hours at room temperature. The mixture is then carefully poured into ice water, extracted with CH2Cl2, and vacuum distilled to yield 2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-chloropropyl)acetonitrile (21, b.p. 160°-165°/0.05 mmHg).

Aufarbeitung

  1. temperaturethe resulting mixture warmed to 80°-90° C. for one hour
  2. extractionextracted with CH2Cl2, and vacuum
  3. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-868cc059f530450f86ebfa8b8426f165
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04667038

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