Dimethylformamide → 4-Bromo-2,2-diphenylbutyric chloride

HRID 279077

Reaktionsgleichung

Reaktionsgleichung von HRID 279077
[Br:1][CH2:2][CH2:3][C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5](O)=[O:6].S(Cl)([Cl:22])=O.CN(C)C=O>C(Cl)(Cl)Cl>[Br:1][CH2:2][CH2:3][C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([Cl:22])=[O:6]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 27569594-Bromo-2,2-diphenylbutyric acid

Produkt 1

HCID 222500664-Bromo-2,2-diphenylbutyric chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In 5 mL of chloroform was suspended 5.00 g (15.7 mmol) of 4-bromo-2,2-diphenylbutyric acid. Thionyl chloride (10 mL) was then added dropwise at room temperature. To the resulting mixture was added 0.1 mL of dimethylformamide, followed by heating under reflux for 5 hours. After completion of the reaction, the solvent was concentrated under reduced pressure, whereby 4-bromo-2,2-diphenylbutyric chloride was obtained. While stirring under ice cooling, 50 mL of cold methanol was added. The temperature was allowed to rise back to room temperature, and then stirring was conducted for 30 minutes. The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 5.00 g (yield: 95.7%) of methyl 4-bromo-2,2-diphenylbutyrate was obtained.

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. customAfter completion of the reaction
  4. concentrationthe solvent was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-249d93f2ca6e439a9e0194fd75c26ef6
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362203B1

Verknüpfte Notizen

Wird geladen…