1,4-Dibromobenzene → HCID 13765572, Verbindung

HRID 1731485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1731485
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:8]=[C:9]([C:16](Cl)=O)[CH:10]=[C:11]([CH:15]=2)[C:12](Cl)=O)=[CH:4][CH:3]=1.CC1C=C(C=C(C)C=1)[O-].[K+].BrC1C=CC(Br)=CC=1.[OH-].[K+]>[Cu]>[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:15]=[C:11]([CH3:12])[CH:10]=[C:9]([CH3:16])[CH:8]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 78041,4-DibromobenzeneHCID 14797Potassium HydroxideHCID 137655745-(4-Bromophenoxy)benzene-1,3-dicarbonyl dichlorideHCID 23666958HCID 23666958, Verbindung

Produkt 1

HCID 13765572HCID 13765572, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23978CopperKatalysator

Versuchsvorschrift

The synthetic route to 5-(4-bromophenoxy)isophthaloyl chloride is depicted in Equation II below. Potassium 3,5-dimethylphenoxide (1.0 mole) was reacted with 1,4-dibromobenzene (2.0 moles) in the presence of copper at 200° C. under nitrogen for two hours. The hot reaction mixture was poured into aqueous potassium hydroxide and subsequently filtered. The resulting oily filtrate was extracted with methylene chloride and the organic phase was washed with water. The methylene chloride was removed and the residue was distilled under vacuum to provide 1-(4-bromophenoxy)-3,5-dimethylbenzene as a colorless liquid in 60% yield. 1-(4-Bromophenoxy)-3,5-dimethylbenzene was oxidized with potassium permanganate (6:1 molar ratio) in a 1:1 mixture of pyridine and water at 90° C. for six hours. The brown reaction mixture was filtered and the filtrate was acidified to afford 5-(4-bromophenoxy)isophthalic acid (m.p. 310°-320° C.) in 80% crude yield. The dicarboxylic acid was refluxed in excess thionyl chloride containing a few drops of N,N-dimethylformamide for six hours. The excess thionyl chloride was removed under vacuum to yield an orange residue which was recrystallized twice from heptane to afford 5-(4-bromophenoxy)isophthaloyl chloride as pale yellow crystals, m.p. 80°-81° C.

Aufarbeitung

  1. filtrationsubsequently filtered
  2. extractionThe resulting oily filtrate was extracted with methylene chloride
  3. washthe organic phase was washed with water
  4. customThe methylene chloride was removed
  5. distillationthe residue was distilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6849e1c990374ea49761ce484729bb1d
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04622182

Notizen zur Reaktion

Wird geladen…