Boron tribromide → HCID 86685155, compound

4-[(5-bromo-2-chloro-phenyl)methyl]-1-ethoxy-2-fluoro-benzene 4e (31.7 g, 92.3 mmol) was dissolved in 300 mL dichloromethane, followed by addition of boron tribromide (11.4 mL, 120 mmol) in an ice bath, then the reaction mixture was warmed and stirred for 4 hours. Thereafter, the reaction mixture was extracted with ethyl acetate (100 mL×4) after 300 mL saturated sodium carbonate solution was dropwise added slowly. The organic extract was washed with saturated sodium chloride solution (30 mL) and combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography with elution system D to obtain the title compound 4-[(5-bromo-2-chloro-phenyl)methyl]-2-fluorophenol 8a (28.1 g, white solid), yield: 96.7%. 1H NMR (400 MHz, CDCl3): δ 7.36-7.18 (m, 3H), 7.01-6.80 (m, 3H), 5.08 (br, 1H), 3.99 (s, 2H).

1. temperaturethe reaction mixture was warmed
2. extractionThereafter, the reaction mixture was extracted with ethyl acetate (100 mL×4) after 300 mL saturated sodium carbonate solution
3. additionwas dropwise added slowly
4. extractionThe organic extract
5. washwas washed with saturated sodium chloride solution (30 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure
9. customThe resulting residue was purified by silica gel chromatography with elution system D

ORD record

ord-9ef5961f65c04ba5ac29b8ad6e71173a

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609622B2