Boron trifluoride etherate → 4-Bromo-1-chloro-2-[[4-(trifluoromethoxy)phenyl]methyl]benzene

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Reaction Steps

(5-bromo-2-chloro-phenyl)-[4-(trifluoromethoxy)phenyl]methanol 6g (4.37 g, 11.5 mmol) was dissolved in 35 mL dichloromethane, followed by addition of triethyl silane (5.49 mL, 34.4 mmol) and dropwise addition of boron trifluoride etherate (2.9 mL, 22.9 mmol). The reaction mixture was stirred for 16 hours. Thereafter, the reaction mixture was concentrated under reduced pressure and partitioned after 20 mL saturated sodium bicarbonate solution were added. The aqueous phase was extracted with dichloromethane (25 mL×3) and the organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography with elution system C to obtain the title compound 4-bromo-1-chloro-2-[[4-(trifluoro-methoxy)phenyl]methyl]benzene 6h (3.0 g, colourless grease), yield: 71.6%. 1H NMR (400 MHz, CDCl3): δ 7.33-7.29 (m, 2H), 7.26-7.24 (m, 1H), 7.21-7.18 (m, 2H), 7.15 (d, 2H), 4.06 (s, 2H).

Provenance & Evidence