Sodium Iodide → Ethyl 3-phenylprop-2-enoate

Participants

Reaction Conditions

Reaction Steps

Chlorobenzene (2825 mg, 25 mmoles), NiBr2 (1095 mg, 5 mmoles), NaI(4125 mg, 27.5 mmoles) and PPh3 (2620 mg, 10 mmoles) were mixed in DMF (20 ml) and heated in 40° C. oil bath for 5 h. The mixture was cooled and treated with ethyl acrylate (2750 mg, 27.5 mmoles), Et3N (2778 mg, 27.5 mmoles), palladium diacetate (56 mg, 0.25 mmoles), and PPh3 (262 mg, 1 mmole). The mixture was heated in a 140° C. oil bath for 18 h. The crude reaction mixture was mixed with Et2O, filtered and washed three times with 50 ml of water. The organic fraction was dried over MgSO4, the solvent was removed on the rotary evaporator and the residue purified by radial chromatography (5:1 volume mixture of hexane and Et2O, two purifications) to give 1700 mg (39% isolated yield) of ethyl cinnamate as a light yellow oil.

Provenance & Evidence