Thionyl Chloride → 5-Bromo-2,4-dimethoxybenzoyl chloride

HRID 1967447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1967447
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].S(Cl)([Cl:17])=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([Cl:17])=[O:8]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 135050975-Bromo-2,4-dimethoxybenzoic acid

Produkt 1

HCID 135050985-Bromo-2,4-dimethoxybenzoyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Under a nitrogen atmosphere, 5-bromo-2,4-dimethoxybenzoic acid (40.0 g) was suspended in toluene solution (DMF concentration: 300 ppm, 200 mL). To the suspension was added dropwise thionyl chloride (21.9 g) at 75° C. After stirring at 75° C. for 1 hr, completion of the reaction was confirmed by HPLC. Toluene and excess thionyl chloride were evaporated under reduced pressure. Toluene (100 mL) was added to the concentrated residue, and the mixture was concentrated again under reduced pressure. THF (100 mL) was added to the obtained 5-bromo-2,4-dimethoxybenzoic acid chloride, which was directly used in the next step.

Aufarbeitung

  1. customToluene and excess thionyl chloride were evaporated under reduced pressure
  2. additionToluene (100 mL) was added to the concentrated residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. additionTHF (100 mL) was added to the obtained 5-bromo-2,4-dimethoxybenzoic acid chloride, which

Quellen und Nachweise

ORD-Eintrag
ord-e0e3d20ee74a4a729e4c0e64db93c569
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420821B2

Notizen zur Reaktion

Wird geladen…