Dichloromethane → 3-(2,3'-Diisobutyl-4'-methoxy-biphenyl-4-yl)propionitrile

Participants

Reaction Conditions

Reaction Steps

294.8 mg (0.88 mmol) 4-(2-Cyanoethyl)-2-isobutylphenyl-trifluormethanesulfonate (6), 312.9 mg (1.08 mmol, 1.23 eq.) 2-(3-Isobutyl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (11) and 156 mg (135 μmol, 0.15 eq.) Pd(Ph3P)4 were dissolved in 20 ml DME/EtOH (9+1). To this yellow solution 0.88 ml (1.76 mmol, 2.00 eq.) of a 2 M aq. Na2CO3-solution was added and the resulting mixture was heated at 80° C. for 17 h. After concentrating the mixture in vacuo the residue was taken up in water and extracted with CH2Cl2. The comb. org. fractions were dried over MgSO4 and evaporated. Colunm chromatography (CH2Cl2) yielded 305.9 mg (0.88 mmol, 99.45%) 3-(2,3′-Diisobutyl-4′-methoxy-biphenyl-4-yl)propionitrile (73) as a clear oil. Rf (CH2Cl2)=0.68. 1H-NMR (500 MHz, CDCl3): δ=0.67 (d, 6H, J=6.62 Hz, 2*CH3), 0.85 (d, 6H, J=6.62 Hz, CH2), 2.59 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.91 (t, 2H, J=7.41 Hz, CH2CH2CN), 3.79 (s, 3H, OCH3), 6.80 (d, 1H, J=8.36 Hz), 6.94 (d, 1H, J=2.21 Hz), 6.98-7.04 (m, 3H), 7.09 (d, 1H, J=7.57 Hz). MS (EI): m/z=350 (23), 349 (90), 307 (10), 306 (35), 290 (39), 250 (15), 248 (17), 247 (100), 246 (24), 209 (21), 191 (16), 178 (10), 174 (10), 147 (10), 145 (17), 144 (19), 117 (13), 105 (25), 83 (11), 57 (18). HR-MS (EI): Calcd. for C24H31NO: 349.240564. Found: 349.240765.

Provenance & Evidence