4-Bromophenacyl bromide → 1-(4-Bromophenyl)-2-fluoroethan-1-one
Reaktionsgleichung
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4].[F-:12].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][F:12])=[CH:6][CH:7]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 2-bromo-1-(4-bromophenyl)-1-ethanone (8.54 g, 30.7 mmol), potassium fluoride (8.92 g, 153 mmol) and 18-crown-6 ether (4.06 g, 15.3 mmol) in acetonitrile (170 ml) was refluxed for 7 hr. After evaporation, the mixture was dissolved in ethyl acetate (300 ml), washed with water (100 ml×2), and dried over magnesium sulfate. Removal of solvent gave 6.8 g of brown solid, which was chromatographed on a column of silica gel (600 g) eluting with ethyl acetate/hexane (1:10) to afford 5.00 g (75%) of the title compound as a pale yellow solid.