Phenacyl bromide → 2-(2-Bromophenoxy)-1-phenylethan-1-one

Reaktionsgleichung

[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[CH2:11](Br)[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]>O1CCCC1>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][C:12](=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

Versuchsvorschrift

(1)-(i) A suspension of 6.72 g of 60% sodium hydride in 40 ml of tetrahydrofuran is added dropwise to a solution of 24.17 g of 2-bromophenol in 210 ml of tetrahydrofuran at 4° C. and the mixture is stirred at the same temperature for 15 minutes. A solution of 30.66 g of phenacyl bromide in 60 ml of tetrahydrofuran is added dropwise to the mixture. The mixture is stirred at the same temperature for 30 minutes and further refluxed for 2.5 hours. The reaction mixture is evaporated to remove solvent, and water is added to the residue. The aqueous mixture is extracted with ethyl acetate and the extract is washed, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography and recrystallized from a mixture of ethyl acetate and n-hexane to give 21.49 g of (2-bromophenyl)(benzoylmethyl)ether as colorless needles.