Hydrochloric Acid → (3-Bromophenyl)(3-methylazulen-1-yl)methanone

HRID 1375964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375964
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[C:15]2[C:9]([CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:8][CH:7]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21].Cl>C(Cl)Cl>[Br:16][C:17]1[CH:18]=[C:19]([C:20]([C:8]2[C:9]3[C:15]([CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:6]([CH3:5])[CH:7]=2)=[O:21])[CH:23]=[CH:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 74377Benzoyl chloride, 3-bromo-HCID 1366111-MethylazuleneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 23080591(3-Bromophenyl)(3-methylazulen-1-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Aluminum chloride (1.87 g) was added to a solution of 1-methylazulene (2 g) in methylene chloride (20 ml) at 0° C. and the mixture was stirred for 15 minutes. Then, a solution of 3-bromobenzoyl chloride (1.86 ml) in methylene chloride (5 ml) was added dropwise to the reaction mixture at 0° C. and the mixture was stirred for one hour. The reaction mixture was added to 10% aqueous solution of hydrochloric acid under cooling with ice and was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain (3-bromophenyl)(3-methylazulen-1-yl)methanone (1.2 g).

Aufarbeitung

  1. stirringthe mixture was stirred for one hour
  2. temperatureunder cooling with ice
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9d01ea02f70642b4932f1211be59625e
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169761B2

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