Water → 3-(3'-Benzyl-4'-hydroxy-2-isobutyl-1,1'-biphenyl-4-yl)propanenitrile

Participants

Reaction Conditions

Reaction Steps

2.20 ml (2.20 mmol, 3 eqv) of a 1 M solution of BBr3 in CH2Cl2 was added to a solution of 279 mg (0.73 mmol) 3-(3′-Benzyl-2-isobutyl-4′-methoxy-1,1′-biphenyl-4-yl)propanenitrile (24) in 12 ml dry CH2Cl2 at 0° C. via syringe. After that, the solution was stirred for 2 h at 0° C. and then for 7 h at rt. 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 258.5 mg (0.70 mmol, 96%) 25 as a pale yellow oil: Rf (Hexanes/EtOAc (2+1)) 0.53; 1H NMR (500 MHz, CDCl3) δ 0.65 (d, 6H, J=6.62 Hz), 1.57 (m, 1H), 2.38 (d, 2H, J=7.25 Hz), 2.57 (t, 2H, J=7.41 Hz), 2.89 (t, 2H, J=7.41 Hz), 3.95 (s, 2H), 4.62 (s, br., 1H), 6.74 (d, 1H, J=8.04 Hz), 6.94-7.24 (m, 10H); LRMS (EI) m/z 369 (8), 335 (10), 293 (15), 161 (13), 160 (66), 91 (35), 86 (63), 84 (100); HRMS (EI) Calcd. for C26H27NO: 369.209264. Found: 369.209026.

Provenance & Evidence