1-(1,1'-Biphenyl)-4-yl-2-bromoethanone → HCID 85717302, Verbindung

Beteiligte Stoffe

Reaktionsschritte

Under an argon atmosphere, 1.65 g (1 0 mmol) of 2-amidino-acetic acid ethyl ester hydrochloride (for preparation see: Liebigs Ann. Chem., 1895 (1977)) are introduced into 10 ml of ethanol and, at 0-5° C., 0.73 g (10 mmol) of sodium ethanolate is added thereto. The bright yellow suspension is stirred for 20 min and then 1.4 g (5 mmol) of 2-bromo-1-(biphen-4-yl)-ethan-1-one (2-bromo-4'-phenyl-acetophenone; Aldrich; Milwaukee/USA) are added thereto. After 48 hours' stirring at RT, the reaction mixture is concentrated by evaporation and the residue is taken up in ethyl acetate and washed with 3 portions of water and brine. The aqueous phases are extracted twice with ethyl acetate and the organic phases are dried over MgSO4 and concentrated by evaporation. Column chromatography (SiO2 ; ethyl acetate/hexane [1:1]) and stirring in diisopropyl ether/hexane yield the title compound; m.p. 186-188° C.; TLC-Rf =0.17 (ethyl acetate/hexane [1:1]); FAB-MS: (M+H)+ =306.

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