Boron tribromide → ({4-[(6-Hydroxy-3-methyl-2-phenyl-1-naphthalenyl)oxy]phenyl}oxy)acetic acid

Participants

Reaction Steps

To a cold (5° C.) solution of ([(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)oxy]acetic acid (235) (0.150 g, 0.36 mmol) in CH2Cl2 (5 mL) was added BBr3 (0.1 mL, 1.1 mmol) slowly. The reaction mixture was stirred between 5° C. and 20° C. for 2 h and poured into 10% aqueous NaHCO3 (60 mL) slowly. The reaction mixture was extracted with EtOAc (3×75 mL). The combined organic layer was washed with brine (1×50 mL), dried (Na2SO4), and concentrated to afford the crude product. Purification by flash column chromatography using CHCl3 and MeOH as an eluent gave 0.028 g (19%) of the title compound (236) as an off-white solid. A 0.058 g of 5-[(4-hydroxyphenyl)oxy]-7-methyl-6-phenyl-2-naphthalenol was also isolated. 1H NMR (400 MHz, CDCl3): δ 7.62 (d, J=8.8 Hz, 1H), 7.46 (s, 1H), 7.26-7.18 (m, 3H), 7.12-7.09 (m, 2H), 6.92 and 6.90 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 6.65 (d, J=9.2 Hz, 2H), 6.50 (d, J=8.8 Hz, 2H), 4.29 (s, 2H), 2.17 (s, 3H). LCMS (ESI) m/z 401.35 (M+H)+.

Provenance & Evidence