Water → 6-(4-Hydroxy-phenyl)-1-phenyl-naphthalen-2-ol

Reaction equation

C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[CH:9]=2)[C:4]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:3]([OH:2])[CH:12]=[CH:11]3)=[CH:14][CH:15]=1

Participants

Procedure

To a mixture of 2-methoxy-6-(4-methoxyphenyl)-1-phenylnaphthalene (0.36 g, 1.06 mmol) in CH2Cl2 (25 mL) at 0° C. was slowly added boron tribromide (3.2 mL of 1N in CH2Cl2). The mixture wag allowed to warm slowly to room temperature and was stirred overnight. The resulting solution was poured into water (100 mL) and extracted with ethyl acetate (3×150 mL).; The combined, organic layers were washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, evaporation of thesolvent, and purification by silica column chromatography (25% ethyl acetate-hexanes) followed by preparative reverse-phase HPLC and drying under vacuum at 105° C. yielded 0.14 g (42%) of the:title compound as a white solid: mp 142–146° C.; 1H NMR (DMSO-d6): δ 6.86 (2H, d, J=8.50 Hz), 7.26–7.42 (5H, m), 7.48–7.61 (5H, m), 7.84 (1H, d, J=8.96 Hz), 8.02 (1H, d, J=1.46 Hz), 9.52 (2H, s); MS (ESI) m/z 311 (M−H)−.