Hydrochloric Acid → HCID 22619377, compound

Participants

Reaction Steps

p-Bromophenylacetonitrile (50 g), t-butyl acrylate (46 ml), palladium (II) acetate (575 mg) and tri-o-tolylphosphine (3.1 g) are combined with 125 ml triethylamine in a steel pressure reactor and heated at 140° for 16 hours. The reaction mixture is cooled to room temperature and poured into 500 ml 3N hydrochloric acid at 0°. The solids are extracted into ethyl acetate and the ethyl acetate solution is extracted with saturated NaCl solution and dried over magnesium sulfate. The crude product is triturated with ether:hexane (1:1), filtered and dried under vacuum to yield t-butyl p-(cyanomethyl)-phenylacrylate; m.p. 80-82°; NMR (CDCl3): 7.5 (2H,d), 7.32 (2H,d), 6.39 (2H,d), 3.78 (2H,s), 1.52 (9H,s).

Provenance & Evidence