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

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).

1. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate (10 mL)
2. customseparated
3. extractionThe aqueous layer was extracted with dichloromethane (20 mL×2)
4. washThe combined organic layers were washed with saturated brine (30 mL×2)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated in vacuo
8. customthe residue was purified by silica gel chromatography
9. washeluted with PE

ORD record

ord-a2f6208ea3f94f2a87ae82d7540be3b3

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394329B2