Toluene → Dimethyl 2'-cyano-4'-methylbiphenyl-3,5-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

A Parr pressure reactor was charged with dimethyl 5-bromoisophthalate (1.3 g, 4.8 mmol), 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (2.0 g, 5.9 mmol), toluene (25 mL), ethanol (5 mL), cesium carbonate (1.7 g, 5.2 mmol), and water (2.5 mL). The mixture was degassed and purged with nitrogen several times before tetrakis(triphenylphosphine)-palladium(0) (280 mg, 0.24 mmol) was added. The tube was sealed and the mixture was heated at 90° C. overnight. After cooling, the mixture was diluted with EtOAc (200 mL), washed with brine, dried over Na2SO4, and concentrated. The residue was purified via flash chromatography to afford the desired product as a white solid. LC-MS: 310.5 [M+1]+; 1H NMR (400 MHz, CDCl3): 8.75 (s, 1H), 8.39 (d, J=1.6 Hz, 2H), 7.61 (s, 1H), 7.49 (dd, J=1.1, 8.5 Hz, 1H), 7.43 (d, J=7.9 Hz, 1H), 3.98 (s, 6H), 2.46 (s, 3H).

Provenance & Evidence