Hydrochloric Acid → (5-Bromo-2-thienyl)(4-ethylphenyl)methanone

HRID 1012030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012030
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1)[CH3:6].[Br:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1.Cl>ClCCl>[Br:16][C:17]1[S:18][C:19]([C:11]([C:10]2[CH:14]=[CH:15][C:7]([CH2:5][CH3:6])=[CH:8][CH:9]=2)=[O:12])=[CH:20][CH:21]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 138512-BromothiopheneHCID 853684-Ethylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 43462872(5-Bromo-2-thienyl)(4-ethylphenyl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Aluminum chloride (8.9 g) and 4-ethylbenzoylchloride (5.96 g) were added to a solution of 2-bromothiophene (3.2 ml) in dichloromethane (50 ml) at 0° C., and the mixture was stirred for four hours at room temperature. 10% hydrochloric acid was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline solution in order and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated from the filtrate under reduced pressure to give the residue. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain (5-bromo-2-thienyl)(4-ethylphenyl)methanone (8.97 g). Borontrifluoride diethyl ether complex (1.57 ml) and triethylsilane (3.83 ml) were added to a solution of (5-bromo-2-thienyl)(4-ethylphenyl)methanone in acetonitrile (20 ml) at −40° C., and the mixture was stirred for two hours. Aqueous solution of saturated potassium carbonate was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated from the filtrate under reduced pressure to give the residue, and the residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain 2-bromo-(4-ethylbenzyl)thiophene (6.78 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated saline solution in order
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated from the filtrate under reduced pressure
  6. customto give the residue
  7. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a96703d323ad481caf07a0be89f2a70f
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977466B2

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