Water → HCID 11589327, compound

Participants

Reaction Steps

To a cold (5° C.) solution of (2E)-3-(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoic acid (10) (1.10 g, 2.68 mmol) in CH2Cl2 (60 mL) was added BBr3 (0.8 mL, 8 mmol) slowly. The reaction mixture was stirred between 5° C. and 20° C. for 1 h and poured into water (150 mL) slowly. The layers were separated and the aqueous layer was further extracted with EtOAc (3×150 mL). The combined organic layer was washed with brine (1×100 mL) dried (Na2SO4) and concentrated to afford the crude product. Purification by flash column chromatography on silica gel using CHCl3:MeOH as an eluent, gave 0.88 g (83%) of the title compound as an off-white solid. IR (film): 30.58, 1682, 1632, 1599, 1504, 1227, 1165 cm−1. 1H NMR (400 MHz, MeOH-d4): δ 7.60 (d, J=8.8 Hz, 1H), 7.51 (s, 1H), 7.52 (d, J=16.0 Hz, 1H), 7.33 (d, J=8.8 Hz, 2H), 7.27-7.20 (m, 3H), 7.14-11 (m, 3H), 6.96 and 6.94 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 6.57 (d, J=8.4 Hz, 2H), 6.75 (d, J=16.0 Hz, 1H), 2.19 (s, 3H). 13C NMR (100 MHz, MeOH-d4): δ 169.5, 161.3, 156.1, 147.1, 144.78, 136.82, 136.3, 135.9, 130.3, 129.8, 129.5, 127.8, 126.83, 124.0, 123.9, 120.9, 118.1, 115.8, 115.7, 108.6, 20.32. HRMS Calcd for C26H20O4: 397.1440. Found: 397.1439.

Provenance & Evidence