Bicarbonate Ion → 1-[(5-Bromo-2-chloro-phenyl)methyl]-2,3-difluoro-4-methoxy-benzene

To a solution of (5-bromo-2-chloro-phenyl)-(2,3-difluoro-4-methoxy-phenyl)methanone 21e (5.42 g, 14.9 mmol) in acetonitrile (100 mL) were added triethyl silicane (4.8 mL, 29.87 mmol) at 15° C., followed by boron trifluoride diethyl ether (7.4 mL, 59.74 mmol). The mixture was warmed up to room temperature and stirred for 15 hours. To the reaction mixture was added ethyl acetate (4 mL). The mixture was adjusted with saturated aqueous bicarbonate to pH 7, and then partitioned. The combined organic layers were 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/EtOAc(v/v)=20/1 to give the title compound 21f as pale yellow oil (1.34 g, 25.8%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 347.05 [M+H]+; and 1H NMR (400 MHz, CDCl3) δ (ppm): 7.33 (m, 1H), 7.28 (m, 2H), 6.84-6.76 (m, 1H), 6.75-6.62 (m, 1H), 4.05 (s, 2H), 3.91 (s, 3H).

1. custompartitioned
2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationThe filtrate was concentrated in vacuo
5. customthe residue was purified by silica gel chromatography
6. washeluted with PE/EtOAc(v/v)=20/1

ORD record

ord-55bcdf5271da447982560e6e0bcf2973

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394329B2