Boron trifluoride etherate → 1-[(5-Bromo-2-chloro-phenyl)methyl]-2,3-difluoro-4-methoxy-benzene

(5-bromo-2-chloro-phenyl)-(2,3-difluoro-4-methoxy-phenyl)methanol 2d (5.1 g, 14.1 mmol) was dissolved in 40 mL methylene chloride, followed by addition of triethyl silane (6.75 mL, 42.3 mmol) and dropwise addition of boron trifluoride diethyl ether (3.57 mL, 28.2 mmol). The reaction mixture was stirred for 16 hours. Thereafter, the reaction mixture was partitioned after 20 mL saturated sodium carbonate solution were added. The aqueous phase was extracted with dichlormethane (20 mL×3) 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 1-[(5-bromo-2-chloro-phenyl)methyl]-2,3-difluoro-4-methoxy-benzene 2e (3.55 g, white solid), yield: 72.4%. 1H NMR (400 MHz, CDCl3): δ 7.36-7.33 (m, 1H), 7.30-7.27 (m, 2H), 6.81-6.79 (m, 1H), 6.73-6.69 (m, 1H), 4.00 (s, 2H), 3.92 (s, 3H).

1. customThereafter, the reaction mixture was partitioned after 20 mL saturated sodium carbonate solution
2. additionwere added
3. extractionThe aqueous phase was extracted with dichlormethane (20 mL×3)
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-8bd6084b4f1a4ed6899882de4df7cb62

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609622B2