3'-(BENZYLOXY)[1,1'-BIPHENYL]-3-CARBONITRILE synthesis

Yield:893736-89-5 60%

Reaction Conditions:

with barium dihydroxide;tetrakis(triphenylphosphine) palladium⁽⁰⁾ in 1,2-dimethoxyethane;water at 80; for 6 h;

Steps:

6

A degassed mixture of 3-benzyloxy-phenyl bromide (28) (0.2 g, 0.76 mmol), 3- cyanophenylboronic acid (0.223 g, 1.52 mmol), barium hydroxide (0.285 g, 1.67 mmol), Pd(PPh₃)₄ (0.088 g, 0.076 mmol), DME (5 mL) and H₂O (3 mL) was heated (80⁰C) for 6 hours with vigorous stirring under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through a plug of celite. The filtrate was diluted with brine; the organic phase was separated, dried (MgSO₄) and concentrated in vacuo. The residue obtained was purified by flash column chromatography (20% diethyl^? ether-hexane) to give 75 (0.130 g, 60% yield) as a viscous liquid. ¹H NMR (500 MHz, CDCl₃) δ 7.85 (t, J = 2.5 Hz, IH), 7.78 (dt, J = 7.5 Hz, J = 1.5 Hz, IH), 7.63 (dt, J = 8.0 Hz, J = 1.5 Hz, IH), 7.53 (t, J = 8.0 Hz, IH), 7.46 (d, J = 7.5 Hz, 2H)₅ 7.44- 7.37 (m, 3H)₅ 7.35 (t, J = 7.0 Hz, IH), 7.18-7.14 (m, 2H), 7.02 (dd, J = 8.5 Hz₅ J = 2.5 Hz, IH)₅ 5.17 (s, 2H).

References:

WO2008/13963,2008,A2 Location in patent:Page/Page column 81