Triethylamine → 2-Fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile

Participants

Reaction Steps

To the solution of 2-fluoro-5-formylbenzonitrile (0.74 g, 5 mmol) and dimethyl 3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonate (1.2 g, 5 mmol) in THF (30 ml) was added triethylamine (0.7 ml, 5 mmol) dropwise at a temperature of below 15° C., which was then slowly rose to ambient temperature and stirred for overnight. The reaction mixture was concentrated and the residue was added water and stirred for 30 min. The precipitated solid was collected by filtration, washed with water, hexane, and ether, and dried in vacuo to afford the target compound (1.2 g, 92.3%) as a light yellow solid (a 50:50 mixture of E and Z isomers), used in next step without further purification.

Provenance & Evidence