Crystal structure of 2,2-dibromo-1-(4-fluoro-2-(4-fluorophenoxy)phenyl) ethanone, C14H8Br2F2O2

Abstract

Source of materialThem ixture of sodium p-fluorophenol( 1.34 g, 10 mmol), 2,4-difluoroacetophenone (1.56g ,1 0m mol), copper(II)chloride (0.02 g) and toluene (10 mL)was stirred at reflux 2h,and then concentrated under vacuum.After cooling to room temperature, hexamethylene(20 mL)was addedtothe residue, whereafter the organiclayer waswashedwithbrine (5 mL)three times. Subsequently, bromine (3.20 g, 20 mmol) in hexamethylene (5 mL) was added dropwise to the above mentioned solution and stirred for 2ha tr oom temperature, and washed with saturated sodium bisulfite solution (5 mL). The title compound was obtained in 75% yield when the organic layer was washed with water to neutral, dried over MgSO4,stripped under the condition of reduced pressure. Single crystals suitable for X-ray measurements were obtained by slow evaporationofits ethanolsolution at room temperature. ExperimentaldetailsAllh ydrogena toms were positioned geometricallya nd refined using ariding model, with C-H =0.93 or 0.98 Åand with U iso (H) =1.2 times U eq (C). DiscussionRecently, interest in fluorine-containing compounds is continuously growing since fluorinated organic products exhibit unique properties that areofgreat interest foravariety of applications [2,3]. The title compound has been obtained during asearch for new fuorine-containing compounds with better biological activity. In the title structure, all bond lengths are normal [4] and in agood agreement with those reported previously [5][6]. Thea tom F1, O2, C7, C9 and the phenyl ring (C1-C6) arecoplanar. The dihedral angle between the phenyl rings is 73.22°. The bond angle of C2-O2-C9 is 121