Boron trifluoride etherate → HCID 67069134, compound

(5-bromo-2-chloro-phenyl)-(4-ethoxy-3-fluoro-phenyl)methanol 4d (12.7 g, 35.3 mmol) was dissolved in 100 mL dichloromethane, followed by addition of triethyl silicane (16.9 mL, 106 mmol) and dropwise addition of boron trifluoride etherate (8.95 mL, 70.6 mmol). The reaction mixture was stirred for 3 hours. Thereafter, the reaction mixture was partitioned after 50 mL saturated sodium bicarbonate solution were added. The aqueous phase was extracted with ethyl acetate (100 mL×2) and 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 B to obtain the title compound 4-[(5-bromo-2-chloro-phenyl)methyl]-1-ethoxy-2-fluoro-benzene 4e (10 g, pale yellow grease), yield: 82.4%. 1H NMR (400 MHz, CDCl3): δ 7.33-7.27 (m, 3H), 6.95-6.90 (m, 3H), 4.14 (q, 2H), 4.01 (s, 2H), 1.49 (t, 3H).

1. customThereafter, the reaction mixture was partitioned after 50 mL saturated sodium bicarbonate solution
2. additionwere added
3. extractionThe aqueous phase was extracted with ethyl acetate (100 mL×2)
4. extractionthe organic extract
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure
8. customthe resulting residue was purified by silica gel chromatography with elution system B

ORD record

ord-8e7c0196ff4d46758dc70a5ae7ee572b

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609622B2