Acrylonitrile → HCID 118005978, compound

Participants

Reaction Conditions

Reaction Steps

Acrylonitrile (1.6 mL, 41 mmol) was added to a mixture of 9 (1.5 g, 4.1 mmol), Et3N (1.1 mL, 13 mmol), PdCl2(PPh3)2 (0.16 g 0.23 mmol), and dry DMF (15.0 mL) under a nitrogen atmosphere at room temperature. The mixture was heated at 140° C. for 3 h. The reaction mixture was quenched with water and extracted with EtOAc (3×50 mL). The organic layer was sequentially washed with brine (2×75 mL), dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography to give (Z)-3-(3-chloro-5-(2-methoxyphenoxy)phenyl)acrylonitrile (0.17 g, 16%) and (E)-3-(3-chloro-5-(2-methoxyphenoxy)phenyl)acrylonitrile (10) (0.52 g, 45%). 1H NMR (400 MHz, CDCl3) δ 7.27 (s, 1H), 7.19-7.08 (m, 2H), 7.06-6.97 (m, 2H), 6.91 (ddt, J=15.9, 14.2, 4.6 Hz, 3H), 5.80 (dd, J=16.6, 5.2 Hz, 1H), 3.79 (s, 3H).

Provenance & Evidence