Hydrochloric Acid → 5-(4-Bromo-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one

HRID 532534

Reaktionsgleichung

[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:9])[CH2:7][CH2:8][C:2]1=2.[H-].[Na+].C1([O:18][C:19](=O)[C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)C=CC=CC=1.Cl>C1COCC1.O>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]([CH:7]2[CH2:8][C:2]3[S:1][CH:5]=[CH:4][C:3]=3[C:6]2=[O:9])=[O:18])=[CH:21][CH:22]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

5,6-Dihydro-cyclopenta[b]thiophen-4-one (3.34 g, 24.2 mmol) in 40 mL of THF was treated with NaH (60 percent, 1.45 g, 36.3 mmol). After the addition of 4-Bromo-benzoic acid phenyl ester (6.7 g, 24.2 mmol), the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was extracted with ethyl acetate. The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(4-Bromo-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (5.4 g, 16.9 mmol) as yellow solid in 70% yield.

Aufarbeitung

temperatureThe solution was cooled to room temperature
extractionwas extracted with ethyl acetate
customThe organic layer was collected
dry with materialdried over MgSO4(s)
concentrationconcentrated under reduced pressure
customThe resultant precipitate was collected
customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag: ord-c0aa556a7a7648fcb7200d401f633a8e
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08853207B2

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