Boron tribromide → (2E)-3-{4-[(3-Ethyl-6-hydroxy-2-phenyl-1-naphthalenyl)oxy]phenyl}-2-propenoic acid

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Reaction Steps

To a solution of (2E)-3-(4-{[3-ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoic acid (60) (104 mg, 0.25 mmol) in reagent grade CH2Cl2 (10 mL) at −10° C. was added BBr3 (1 M in CH2Cl2, 0.74 mL, 0.74 mmol) dropwise. The mixture was then stirred at −5° C. to 0° C. for 2 h, poured into ice water and extracted with EtOAc. The combined organic extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as reddish brown oil. The crude product was purified by reverse phase preparation HPLC on Agilent 1100 (30% CH3CN in H2O to 100% CH3CN) to give 64 mg (64%) of the title compound (61) as light beige solid. mp 188-190° C. 1H NMR (400 MHz, CH3OH-d4): δ 1.07 (t, J=7.5 Hz, 3H), 2.55 (q, J=7.5 Hz, 2H), 6.26 (d, J=16.0 Hz, 1H), 6.56 (d, J=8.8 Hz, 2H), 6.96 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 7.10-7.16 (m, 3H), 7.18-7.28 (m, 3H), 7.34 (d, J=8.8 Hz, 2H), 7.52 (d, J=16.0 Hz, 1H), 7.53 (s, 1H), 7.59 (d, J=8.9 Hz, 1H). LCMS (ESI): m/z 411 (M+H)+, m/z 409 (M−H)−. HRMS (EI) Calcd for C27H22O4: 411.1596 (M+•). Found: 411.1596.

Provenance & Evidence