Reaction Steps
1.44 ml (1.44 mmol, 3.00 eq.) of a 1 M solution of BBr3 in CH2Cl2 was added to a solution of 270.8 mg (0.48 mmol) 3-(3,2″-Diisobutyl-4-methoxy-2′-naphthalen-1-ylmethyl-[1,1′:4′,1″]-terphenyl-4″-yl)propionitrile (68) in 25 ml dry CH2Cl2 at 0° C. via syringe. After that the solution was stirred for 60 min at 0° C. and then for 12 h at r.t. The reaction mixture was then added to water and extracted with CH2Cl2. The comb. org. fractions were dried over MgSO4 and evaporated. Column chromatography (hexanes/EtOAc (2+1)) yielded 261.9 mg (0.48 mmol, 98.89%) 3-(4-Hydroxy-3,2″-diisobutyl-2′-naphthalen-1-ylmethyl-[1,1′:4′,1″]-terphenyl-4″-yl)propionitrile (69) as a colorless oil. Rf (hexanes/EtOAc (2+1))=0.40. 1H-NMR (500 MHz, CDCl3): δ=0.53 (d, 6H, J=6.62 Hz, 2*CH3), 0.79 (d, 6H, J=6.62 Hz, 2*CH3), 1.47 (m, 1H, CH), 1.73 (m, 1H, CH), 2.24 (d, 2H, J=7.41 Hz, CH2), 2.39 (d, 2H, J=7.09 Hz, CH2), 2.58 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.90 (t, 2H, J=7.41 Hz, CH2C2CN), 4.38 (s, 2H, CH2Naphthyl), 4.58 (s, 1H, OH), 6.76 (d, 1H, J=8.04 Hz), 6.97 (m, 2H), 7.00 (m, 1H), 7.08-7.16 (m, 5H), 7.30-7.41 (m, 4H), 7.67 (dm, 1H, J=8.04 Hz), 7.72 (dm, 1H, J=8.51 Hz), 7.78 (dm, 1H, J=8.04 Hz). MS (EI): m/z=553 (11), 552 (43), 551 (100), 141 (49). HR-MS (EI): Calcd. for C40H41NO: 551.318814. Found: 551.318350.
