Felbinac → HCID 18508082, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of diisopropylamine (0.537 g, 5.31 mmol) in THF (5.2 mL) at 0° C. was added n-butyllithium (2.1 mL, 5.22 mmol, 2.5 M in hexane) dropwise. After stirring for 15 min at 0° C., the mixture was cooled to −78° C. and a solution of 4-biphenylacetic acid (0.500 g, 2.36 mmol) in THF (2 mL) was added dropwise. After again warming to 0° C. and cooling to −78° C., 3-bromo-2-methylproene (0.485 g, 3.54 mmol) was added to the mixture in one portion. After stirring at −78° C. for 1 h, the reaction was quenched with 2 mL of water then concnetrated. The residue was redissolved in water and extracted with ether (100 mL). The aquious layer was acidified (3 N HCl) and extracted with ether (3×100 mL). The organic layers were combined, dried (MgSO4), filtered and concnetrated to yield a white solid (0.449 g, 72%). MS(ESI): 265.3 (M+H)−.

Provenance & Evidence