Boron tribromide → HCID 86685155, compound

Participants

Reaction Steps

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).

Provenance & Evidence