Reaction equation
B(Br)(Br)Br.[CH2:5]([C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]#[N:18])[CH:12]=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[C:21]([CH2:27][CH:28]([CH3:30])[CH3:29])[CH:20]=1)[CH:6]([CH3:8])[CH3:7].O>C(Cl)Cl>[OH:25][C:22]1[CH:23]=[CH:24][C:19]([C:10]2[CH:11]=[CH:12][C:13]([CH2:15][CH2:16][C:17]#[N:18])=[CH:14][C:9]=2[CH2:5][CH:6]([CH3:7])[CH3:8])=[CH:20][C:21]=1[CH2:27][CH:28]([CH3:30])[CH3:29]Participants
Conditions
- Temperature
- 0 °C
Procedure
2.37 ml (2.37 mmol, 3.00 eq.) of a 1 M solution of BBr3 in CH2Cl2 was added to a solution of 275.6 mg (0.79 mmol) 3-(2,3′-Diisobutyl-4′-methoxy-biphenyl-4-yl)propionitrile (73) in 25 ml dry CH2Cl2 at 0° C. via syringe. After that the solution was stirred for 3 h at 0° C. and then for 10 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 174.9 mg (0.52 mmol, 65.99%) 3-(4′-Hydroxy-2,3′-diisobutyl-biphenyl-4-yl)-propionitrile (74) as an oily white solid. Rf (hexanes/EtOAc (2+1)) =0.38. 1H-NMR (500 MHz, CDCl3): δ=0.69 (d, 6H, J=6.62 Hz, 2*CH3), 0.92 (d, 6H, J=6.62 Hz, 2*CH3), 1.63 (m, 1H, CH), 1.93 (m, 1H, CH), 2.45 (d, 2H, J=7.25 Hz, CH2), 2.47 (d, 2H, J=7.25 Hz, CH2), 2.62 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.94 (t, 2H, J=7.41 Hz, CH2CH2CN), 4.60 (s, br., 1H, OH), 6.75 (d, 1H, J=8.36 Hz), 6.92-6.96 (m, 2H), 7.01-7.06 (m, 2H), 7.11 (d, 1H, J=7.57 Hz). MS (EI): m/z=336 (24), 335 (100), 292 (18), 251 (10), 236 (35), 209 (12), 196 (10), 195 (48), 178 (10), 165 (10). HR-MS (EI): Calcd. for C23H29NO: 335.224914. Found: 335.225330.
Workup
- waitfor 10 h at r.t
- extractionextracted with CH2Cl2
- dry with materialfractions were dried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-850670b402ce4c4fa7e9e5a6744a0346
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312246B2
Linked notes
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