(5-Bromo-2-chloro-phenyl)-[4-(trifluoromethoxy)phenyl]methanol → 4-Bromo-1-chloro-2-[[4-(trifluoromethoxy)phenyl]methyl]benzene

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Reaction Steps

To a solution of (5-bromo-2-chloro-phenyl)-[4-(trifluoromethoxy)phenyl]methanol 15f (5.0 g, 13.0 mmol) in dichloromethane (50 mL) was added triethyl silicane (4.57 g, 39.0 mmol) at 0° C., and then boron fluoride ethyl ether (3.72 g, 26.0 mmol) was added slowly. The resulting mixture was allowed to warm up to room temperature and further stirred for 16 hours. The reaction mixture was quenched with saturated aqueous sodium bicarbonate (10 mL), and then separated. The aqueous layer was extracted with dichloromethane (20 mL×2). The combined organic layers were washed with saturated brine (30 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE to give the title compound 15g as colourless oil (3.69 g, 77.0%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ (ppm): 7.34 (dd, 1H), 7.31 (d, 1H), 7.28 (s, 1H), 7.22 (d, 2H), 7.17 (d, 2H), 4.08 (s, 2H).

Provenance & Evidence