Boron trifluoride etherate → HCID 86685118, compound

Participants

Reaction Steps

(5-bromo-2-chloro-phenyl)-(4-ethoxy-2,3-difluoro-phenyl)methanol 3d (8.0 g, 21.2 mmol) was dissolved in 150 mL of mixed solution (acetonitrile and dichloromethane, v:v=2:1), followed by addition of triethylsilane (10.1 mL, 63.6 mmol) and boron trifluoride etherate (5.3 mL, 42.4 mmol). The reaction mixture was stirred for 3 hours, before 100 mL 2 M potassium hydroxide were added. The organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system C to obtain the title compound 1-[(5-bromo-2-chloro-phenyl)methyl]-4-ethoxy-2,3-difluoro-benzene 3e (5.5 g, white solid), yield: 72.4%. MS m/z (ESI): 360.5 [M+1]. 1H NMR (400 MHz, CDCl3): δ 7.36-7.27 (m, 3H), 6.81-6.76 (dd, 1H), 6.72-6.68 (dd, 1H), 4.17-4.13 (q, 2H), 4.10 (s, 2H), 1.50-1.47 (t, 3H).

Provenance & Evidence