Triphenylphosphine → 4-[2-Allyl-2-(4-bromo-phenyl)-pent-4-enyloxy]-4'-trifluoromethyl-biphenyl

Participants

Reaction Steps

A solution of 2-allyl-2-(4-bromo-phenyl)-pent-4-en-1-ol (from Preparation 3, Step B)(0.206 g, 0.734 mmol), 4′-trifluoromethyl-biphenyl-4-ol (0.184 g, 0.772 mmol), and triphenylphosphine (0.286 g, 1.09 mmol) in toluene (7.0 mL) is treated with 1,1′-(azodicarbonyl)-dipiperidine (0.272 g, 1.08 mmol) and stirred overnight at room temperature. The reaction is then warmed to 80° C. for 6 h, cooled to room temperature, diluted with MeOH, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% EtOAc to 50% EtOAc to provide 0.226 g, (61%) of the title compound as a yellow syrup. 1H NMR (CDCl3): δ 7.66-7.61 (m, 4H), 7.52-7.50 (m, 2H), 7.46-7.44 (m, 2H), 7.24-7.22 (m, 2H), 7.00-6.98 (m, 2H), 5.56 (ddt, J=17.1, 10.3, 7.2 Hz, 2H), 5.05-4.99 (m, 4H), 4.12 (s, 2H), 2.61 (d, J=7.4 Hz, 4H).

Provenance & Evidence